Phosphorus-containing polymers for optical signal transducers

• US 7,101,945 B2
• Filed: 02/20/2002
• Issued: 09/05/2006
• Est. Priority Date: 02/22/2001
• Status: Expired due to Fees

• Current Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Original Assignee: Bayer AG
• Inventors: Köhler, Burkhard, Dorn, Ingmar
• Primary Examiner(s): PEZZUTO, HELEN LEE
• Application Number:
  US10/081,628
• Publication Number:
  US 20020114604A1
• Time in Patent Office: 1,658 Days
• Field of Search: 526/274, 526/277, 526/278, 525/327.4, 525/328.2, 525/328.4, 525/328.8, 525/328.9, 525/340
• US Class Current: 526/277
• CPC Class Codes: C08F 230/02 containing phosphorus
• CPC Class Codes: C08F 251/02 on to cellulose or derivatives thereof
• CPC Class Codes: C08F 275/00 Macromolecular compounds obtained by polymerising monomers on to polymers of monomers containing phosphorus, selenium, tellurium or a metal as defined in group C08F30/00
• CPC Class Codes: C08F 8/40 Introducing phosphorus atoms or phosphorus-containing groups
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C09D 151/003 grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds C09D151/04, C09D151/06 take precedence
• CPC Class Codes: C09D 151/02 grafted on to polysaccharides
• CPC Class Codes: C09D 153/00 Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
• CPC Class Codes: G02B 6/1221 made from organic materials
• CPC Class Codes: Y10T 428/29 Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof

Abstract

The invention relates to a phosphorus-containing polymer for coating dielectric materials, to processes for its preparation and to its use, as well as to an optical signal transducer having a coating of the polymer and to its use.

Claims

1. Phosphorus-containing polymer, suitable for coating dielectric surfaces, of the general formula I or II,

P(A)_m(F)_n1(U)_o1 

 

(I)

P(A)_m(UF_n2)_o2 

 

(II)

in which

P stands for a linear or branched, uncrosslinked homo- or heteropolymeric polymer component selected from the group consisting of;

i) polyvinyl alcohols, polyvinyl amine, polyallyl amine, polyethylene imine, imides of polymaleic anhydride-alt-methyl vinyl ether or derivatives thereof;

ii) linear polyethylene glycols, polypropylene glycols or derivatives thereof;

iii) branched or star-branched polyethylene glycols;

iv) polyureas, polyurethanes, polyesters, polycarbonates, polyhydroxycarboxylic acids or derivatives thereof, which are made up of diols/polyols and/or diamines/polyamines;

v) polysaccharides as cellulose, starch, agarose, dextran, chitosan, hyaluronic acid or derivatives thereof;

vi) polypeptides or derivatives thereof which are made of one or more various amino acid; and

vii) branched polyols based on glycidol;

A stands for identical or different phosphorus-containing groups bonded to P,

m stands for a number from 3 to 1000,

F stands for identical or different functional groups bonded directly or indirectly to P, which are present in addition to A,

n1 stands for a number from 1 to 1000,

n2 stands for a number from 1 to 100,

U stands for identical or different, linear or branched, uncrosslinked oligomeric or polymeric segments, made up of identical or different monomers, which are bonded to P,

o1 stands for a number from 0 to 1000,

o2 stands for a number from 1 to 1000.

2. Polymer according to claim 1, wherein said polymer contains phosphorus-containing groups A in an amount of from 0.001 to 10 mEq.

3. Polymer according to claim 1, wherein said polymer contains functional groups F in an amount of from 0.001 to 20 mEq.

4. Polymer according to claim 1, wherein said polymer contains segments U in an amount of from 0.001 to 20 mEq.

5. Polymer according to claim 1, wherein the polymer has a Mw of from 1000 to 10,000,000 g/mol.

6. Polymer according to claim 1, wherein the polymer component P is a statistical copolymer or block copolymer.

7. Polymer according to claim 1, wherein the polymer component P is hydrophilic.

8. Polymer according to claim 1, wherein said polymer contains phosphorus-containing groups A in the form of a spacer carrying from one to six identical or different phosphorus-containing radicals.

9. Polymer according to claim 1, wherein said polymer contains functional groups F that can form covalent bonds, coordination bonds or take part in biochemical recognition reactions.

10. Polymer according to claim 1, wherein said polymer contains functional groups F with crosslinkers.

11. Polymer according to claim 1, wherein the segments U have a Mw of from 100 to 10,000 g/mol.

12. Polymer according to claim 1, wherein the groups or segments U are hydrophilic.

13. Process for preparing a polymer according to claim 1, wherein the polymer component P is bonded to phosphorus-containing group A and optionally oligomeric or polymeric segments U, comprising the step of copolymerizing

(A) a monomer containing a phosphorus-containing group A, or a plurality of identical or different monomers containing identical or different phosphorus-containing groups A

with

(B) a monomer containing a functional group F, or a plurality of identical or different monomers containing identical or different functional groups F, and

(C) optionally, a monomer containing a segment U, or a plurality of identical or different monomers containing identical or different segments U, to form a polymer of the formula I,

or with

(B′ ) a monomer containing a unit (UF₂)_o2 according to formula II, or a plurality of identical or different monomers containing identical or different units of the formula (UF₂)_o2 according to formula II, to form a polymer of the formula II.

14. Process for preparing a polymer according to claim 1, comprising the following steps:

(i) preparing a polymer, which forms the polymer component P and carries identical or different functional groups that are suitable as functional groups F,

(ii) reacting some of the functional groups to form identical or different phosphorus-containing groups A, and

(iii) optionally, reacting some of the functional groups to form identical or different segments U,

wherein step (iii) can be carried out after, before or together with step (ii), and wherein not all the functional groups are converted in steps (ii) and (iii), and the functional groups that are not converted in steps (ii) and (iii) form the functional groups F of the polymer.

15. Process according to claim 14, wherein some or all of the functional groups that have not been converted in steps (ii) and (iii) are reacted with one or more identical or different crosslinkers to form functional groups F.

16. Polymer according to claim 1, wherein said polymer contains phosphorus-containing groups A in an amount of from 00.1 to 5 mEq.

17. Polymer according to claim 1, wherein said polymer contains phosphorus-containing groups A in an amount of from 0.1 to 3 mEq.

18. Polymer according to claim 1, wherein said polymer contains functional groups F in an amount of from 0.01 to 10 mEq.

19. Polymer according to claim 1, wherein said polymer contains functional groups F in an amount of from 0.5 to 10 mEq.

20. Polymer according to claim 1, wherein said polymer contains segments U in an amount of from 0.01 to 10 mEq.

21. Polymer according to claim 1, wherein said polymer contains segments U in an amount of from 0.5 to 10 mEq.

22. Polymer according to claim 1, wherein the polymer has a Mw of from 2100 to 1,000,000 g/mol.

23. Polymer according to claim 1, wherein the polymer has a Mw of from 5000 to 500,000 g/mol.

24. Polymer according to claim 1, wherein the polymer has a Mw of from 5000 to 300,000 g/mol.

25. Polymer according to claim 1, wherein the polymer has a Mw of from 10,000 to 150,000 g/mol.

26. Process for preparing a polymer according to claim 1, comprising the following steps:

(i) preparing a polymer, which forms the polymer component P and carries identical or different functional groups that are suitable as functional groups F, said functional groups F being selected from the group consisting of hydroxyl groups, carboxyl groups, derivatives of carboxyl groups and amine groups,

(ii) reacting some of the functional groups to form identical or different phosphorus-containing groups A, and

(iii) optionally, reacting some of the functional groups to form identical or different segments U,

wherein step (iii) can be carried out after, before or together with step (ii), and wherein not all the functional groups are converted in steps (ii) and (iii), and the functional groups that are not converted in steps (ii) and (iii) form the functional groups F of the polymer.

27. The polymer of claim 1, wherein in polymer component P, the diols/polyols are polyethylene glycols or polypropylene glycols.

28. The polymer of claim 1, wherein in polymer component P, the diamines/polyamines are jeffamine, polyethylene imines, polyvinyl amine, polyallyl amine or polyethylene imine.

29. The polymer of claim 1, wherein in polymer component P, the polysaccharide derivatives are hydroxyalkyl derivatives or acid semiesters.

30. The polymer of claim 1, wherein in polymer component P, the polypeptides are selected from the group consisting of polylysine, polyphenylalanine-lysine, polyglutamates, polymethylglutamate-glutamate, polyphenylalanine-glutamate, polyserine, polyglycine and polyserine-glycerine.

31. The polymer of claim 1, wherein in polymer component P, the branched polyols based on glycidol are polyols based on glycidol with a degree of polymerization of 1 to 300, a polydispersity index below 1.7, a content of branched units, based on the sum of all monomeric units and determined by ¹³C NMR spectroscopy, of 10 to 33 mol %.