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US 10,208,031 B2Granted
Photocrosslinkable materials comprising alicyclic group
AssigneeRolic AG
InventorsJean-Francois Eckert, Guy Marck, Oliver Muller
Life of this patent
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Abstract
A diamine compound of formula (I) is proposed as well as polymers, copolymers, polyamic acids, polyamic acid esters, or polyimides based on such compound.
Claims25
Polymer, copolymer or oligomer comprising, as one basic building block, a diamine compound of formula (I):
- wherein,
- A represents an unsubstituted or substituted phenylene;
- and wherein when A represents a substituted phenylene, the phenylene is substituted by at least one of a halogen atom, an acryloyloxy group, a methacryloyloxy group, an alkoxy group, an alkylacryl group, an alkylmethacryl group, an acrylenacryl group, a methacrylenalkyl group, an alkylcarbonyloxy group, and an alkyloxycarbonyl group, wherein the alkyl residue has from 1 to 10 carbon atoms;
- B represents a straight-chain or branched C1-C12alkyl group or a C1-C12 fluoroalkyl group, wherein one or more —CH2— group may independently from each other be replaced by a linking group selected from —O—, —CO—, —COO—, —OCO—, —NR1—, —NR1CO—, —CONR1—, and —CH═CH—;
- and wherein:
- R1 represents a hydrogen atom or C1-C6alkyl;
- with the proviso that oxygen atoms are not directly linked to each other;
- Q represents an alicyclic group selected from the group consisting of cyclohexyl and bicyclo [2.2.2] octane;
- D is selected from the group consisting of the following compounds:
- wherein
- L, L1, L2 and L3 are independently from each other —CH3, —COCH3, —OCH3, nitro, cyano, halogen, CH2═CH—, CH2═C(CH3)—, CH2═CH—(CO)O—, CH2═CH—O—, —NR5R6, CH2═C(CH3)—(CO)O— or CH2═C(CH3)—O—,
- T, T1, T2 and T3 are independently from each other a substituted or unsubstituted straight-chain or branched C1-C20alkylene group, in which one or more —CH2— group(s) may independently from each other be replaced by a non-aromatic unsubstituted or substituted carbocyclic or heterocyclic group, or a heteroatom and/or by a bridging group selected
- from —CH(OH)—, —CO—, —CH2(CO)—, —SO—, —CH2(SO)—, —SO2—, —CH2(SO2)—, —COO—, —OCO—, —COCF2—, —CF2CO, —S—CO—, —CO—S—, —SOO—, —OSO—, —SOS—, —O—CO—O, —CH2—CH2—, —OCH2—, —CH2O—, —CH═CH—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —CH═N—, —C(CH3)═N—, —N═N— or a single bond;
- or a cyclic, straight-chain or branched, substituted or unsubstituted C1-C24alkylene, wherein one or more —CH2— group may independently from each other be replaced independently from each other by a linking group selected from —O—, —CO, —CO—O—, —O—CO—, —NR1—, —NR1—CO—, —CO—NR1—, —NR1—CO—O—, —O—CO—NR1—, —NR1—CO—NR1—, —CH═CH—, —C≡C—, —O—CO—O—, and —Si(CH3)2—O—Si(CH3)2—, and wherein:
- R1 represents a hydrogen atom or C1-C6alkyl;
- with the proviso that oxygen atoms of linking groups are not directly linked to each other, which is at least once linked to at least one group S1 in formula (I);
- M represents H, C1-C6alkyl, CF3,
- “—” is a single bond,
- q is an integer of 1 or 2;
- and
- q1, q2 and q3 are independently from each other an integer from 0 to 2;
- m is an integer of 1 or 2;
- m1, m2 and m3 are independently from each other an integer from 0 to 2;
- u3, u3′ and u3″ are independently from each other an integer from 0 to 2;
- R5, R6 each independently from each other represents a hydrogen atom or C1-C6alkyl;
- Z4 represents an unsubstituted straight-chain or branched C1-C20alkylene group, in which one or more —CH2— group may independently from each other be replaced by a non-aromatic or aromatic unsubstituted carbocyclic or heterocyclic group;
- and/or a heteroatom and/or by a bridging group selected
- from —CH(OH)—, —CO—, —CH2(CO)—, —SO—, —CH2(SO)—, —SO2—, —CH2(SO2)—, —COO—, —OCO—, —COCF2—, —CF2CO, —S—CO—, —CO—S—, —SOO—, —OSO—, —SOS—, —O—CO—O, —CH2—CH2—, —OCH2—, —CH2O—, —CH═CH—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —CH═N—, —C(CH3)═N—, —N═N— or a single bond;
- or a cyclic, straight-chain or branched, unsubstituted C1-C24alkylene, wherein one or more —CH2— group may independently from each other be replaced independently from each other by a linking group selected from —O—, —CO—, —CO—O—, —O—CO—, —NR1—, —NR1—CO—, —CO—NR1—, and —CH═CH—, and
- wherein:
- R1 represents a hydrogen atom or C1-C6alkyl;
- with the proviso that oxygen atoms of linking groups are not directly linked to each other;
- and wherein
- D is at least once linked to at least one group S1 in formula (I) via a single bond “—”;
- or
- via a side chain T, T1, T2 or T3;
- or via group Z4;
- with the proviso that
- u3+q, or u3+m is ≤4;
- u3+q1 and/or u3′+q2 or/and u3+m1, or/and u3′+m2, or/and u3″+q3, or/and
- u3″+m3 is ≤4;
- q1+q2, and m1+m2;
- and q1+q2+q3, and m1+m2+m3 is >1;
- E represents an aromatic group or an oxygen atom;
- S1 represents a single bond or a straight-chain C1-C8alkylene group, wherein one —CH2— group may be replaced by —O—, —OCO—, —COO—, —NR1CO—, —CONR1—, wherein R1 is hydrogen or C1-C6alkyl;
- S2 represents a single bond or —COO— or —OCO—;
- X, Y represents hydrogen;
- n1 represents 1, 2, 3 or 4;
- n represents 1, 2, 3 or 4;
- with the proviso that if n is 2, 3, or 4, each A, B, Q, D, E, S1, S2, X, Y are identical or different;
- and if n1 is 2, 3 or 4 each B, Q is identical or different;
- wherein the polymer, copolymer or oligomer is a polyamic acid or polyimide;
- wherein the polymer, copolymer or oligomer comprises between 3 and 200 repeating units;
- and wherein the polymer, copolymer or oligomer is formed by reacting monomers of formula (I) with at least one cycloaliphatic tetracarboxylic acid dianhydride.
51 more elements
Dependencies are inferred from the claim text.