Bis(dialkylmaleimide) derivative and polyetherimide for optical communications formed therefrom

• US 6,077,928 A
• Filed: 12/30/1998
• Issued: 06/20/2000
• Est. Priority Date: 12/31/1997
• Status: Expired due to Fees

• Current Assignee: Samsung Electronics Co. Ltd.
• Original Assignee: Samsung Electronics Co. Ltd.
• Inventors: Chung, Eun-young, Rhee, Tae-hyung, Suh, Dong-hack
• Primary Examiner(s): Hempton-Hightower, P.
• Application Number:
  US09/223,313
• Time in Patent Office: 538 Days
• Field of Search: 548/462, 528/310, 528/170, 528/322, 528/332
• US Class Current: 528/170
• CPC Class Codes: C07D 207/444 having two doubly-bound oxygen atoms directly attached in positions 2 and 5
• CPC Class Codes: C07D 207/452 with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 207/456 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
• CPC Class Codes: C08G 73/123 the unsaturated precursors comprising halogen-containing substituents
• CPC Class Codes: C08G 73/126 the unsaturated precursors being wholly aromatic
• CPC Class Codes: C08L 79/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
• CPC Class Codes: G02B 1/046 characterised by the core material
• CPC Class Codes: G02B 2006/12069 Organic material
• CPC Class Codes: G02B 6/02033 Core or cladding made from organic material, e.g. polymeric material G02B1/04 takes precedence

Abstract

A bis(disubstitutedmaleimide) derivative and a polyetherimide for optical communications and the polyetherimide formed therefrom are described. The polyetherimde has a high refractive index, so that when using such polyetherimide as a material for a core of an optical fiber, the range of the materials that can be selected for the cladding becomes wide. Also, a coating property and adhesion to a substrate are improved, thereby providing a good film forming property and thermal stability. Also, because the polyetherimide can minimize optical loss at a near infrared wavelength range, the polyetherimide is very useful as an optical material in the optical communications field adopting the light of near infrared wavelength.

Claims

1. A composition of matter, comprising a bis(disubstitutedmaleimide) derivative represented by the chemical formula:

##STR6## where each of X₁, X₂, X₃ and X₄ is independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ring group, NO₂, --OR¹ and --SR¹ (where R¹ is halogenated alkyl or halogenated aromatic ring group);

and Z₁ is selected from the group consisting of divalent fully halogenated aliphatic hydrocarbon, divalent fully halogenated aliphatic cyclic hydrocarbon and divalent fully halogenated aromatic hydrocarbon.

2. The composition of matter of claim 1, where X₁ is selected from the group consisting of partially or perchlorinated alkyl groups, partially or perchlorinated aromatic ring groups, partially or perchlorinated alkoxy groups, and partially or perchlorinated phenoxy groups;

and

where X₂, X₃ and X₄ are the same as X₁.

3. The composition of matter of claim 1, wherein Z₁ is selected from the group consisting of divalent fully halogenated aliphatic hydrocarbon of C₁ -C₂₅, divalent fully halogenated aliphatic cyclic hydrocarbon of C₁ -C₂₅ and divalent fully halogenated aromatic hydrocarbon of C₆ -C₂₅.

4. A composition of matter, comprising a bis(disubstitutedmaleimide) derivative represented by the chemical formula:

##STR7## where each of X₁, X₂, X₃ and X₄ is independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ring group, NO₂, --OR¹ and --SR¹ (where R¹ is halogenated alkyl or halogenated aromatic ring group);

and Z₁ is a divalent fully substituted aromatic compound.

5. The composition of matter of claim 4,

where Z₁ is selected from the group represented by the structural formula:

##STR8## where Y₁, Y₂, Y₃ and Y₄ are independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ring group, NO₂, --OR¹ and --SR¹ (where R¹ is a halogenated alkyl or halogenated aromatic ring group).

6. The composition of matter of claim 4,

where Z₁ is selected from the group represented by the structural formula:

##STR9## where Y₁, Y₂, Y₃, Y₄, Y₅ Y₆, Y₇ and Y₈ are independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ring group, NO₂, --OR¹ and --SR¹ (where R¹ is halogenated alkyl or halogenated aromatic ring group); and

Q represents either a single bond or is a radical selected from the group consisting of --O--, --CO--, --SO₂ --, --S--, --(OT)_m --, --(OT)_m -- and --(OT)_m --, where T is halogenated alkylene or halogenated arylene group and m is an integer from 1 to 10.

7. A polymer for use in optical communications, comprising a repeating unit represented by the chemical formula:

##STR10## wherein X₁ and X₄ are independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ring group, NO₂, --OR¹ and --SR¹ (where R¹ is halogenated alkyl or halogenated aromatic ring group); and

Z₁ and Z₂ are independently selected from the group consisting of divalent halogenated aliphatic hydrocarbon, divalent halogenated aliphatic cyclic hydrocarbon and divalent halogenated aromatic compound.

8. The polymer of claim 7, wherein X₁ and X₄ are independently and selected from the group consisting of chloride atom, partially or perchlorinated alkyl groups, partially or perchlorinated aromatic ring groups, partially or perchlorinated alkoxy groups, and partially or perchlorinated phenoxy groups.

9. The polymer of claim 7, wherein Z₁ and Z₂ are independently selected from the group consisting of divalent halogenated aliphatic hydrocarbon of C₁ -C₂₅, divalent halogenated aliphatic cyclic hydrocarbon of C₁ -C₂₅ and divalent halogenated aromatic hydrocarbon of C₆ -C₂₅.

10. The polymer of claim 7, wherein Z₁ and Z₂ are independently selected from the group represented by the following structural formula:

##STR11## wherein Y₁, Y₂, Y₃ and Y₄ are independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ling group, NO₂, --OR¹ and --SR¹ (where R¹ is halogenated alkyl or halogenated aromatic ring group).

11. The polymer of claim 7, wherein Z₁ and Z₂ are independently selected from the group represented by the following structural formula:

##STR12## wherein Y₁, Y₂, Y₃, Y₄, Y₅, Y6, Y₇ and Y₈ are independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ring group, NO₂, --OR¹ and --SR¹ (where R¹ is halogenated alkyl or halogenated aromatic ling group); and

Q is a simple chemical bond or selected from the group consisting of --O--, --CO--, --SO₂ --, --S--, --(OT)_m --, --(OT)_m -- and --(OT)_m -- (where T is halogenated alkylene or halogenated arylene group and m is an integer from 1 to

     10).

12. The polymer of claim 7, where the polymer has a molecular weight of 1×

10⁴ ˜

4.5×

10⁴ Dalton.

13. The polymer of claim 7, where the polymer has a thermal decomposition temperature of 300˜

500°

C.

14. The polymer of claim 7, where the polymer has a glass transition temperature of 220˜

320°

C.

15. A polymer prepared by the process of polymerization of a bis(disubstitutedmaleimide) derivative with a diol, where:

said bis(disubstitutedmaleimide) derivative is selected from the group consisting of 2,3,5,6-tetrafluorobenzenebis(dichloromaleimide), 2,3,5,6-tetrachlorobenzenebis(dichloromaleimide), octafluorobiphenylbis(dichloromaleimide), 2,2'"'"'-bis(trichloromethyl)-4,4'"'"'-bis(dichloromaleimide)hexafluorobiphenyl, bis(4-dichloromaleimidetetrafluorophenyl)difluoromethane, 2,4-bis (trifluoromethyl)difluoro-1,3-phenylenebis(dichloromaleimide), bis(dichloro-4-maleimide) and bis(3,4-dichloromaleimide)octafluorobiphenylsulfone.

16. A polymer prepared by the process of polymerization of a bis(disubstitutedmaleimide) derivative with a diol, where:

said diol is selected from the group consisting of tetrafluorohydroquinone, tetrachlorohydroquinone, 2,2-bis(4-hydroxyphenyl)hexachloropropane, 4,4'"'"'-dihydoroxydiphenylether, 4,4'"'"'-dihydroxydiphenylsulfone, 4,4'"'"'-dihydroxy-3,3 '"'"',5,5'"'"'-tetrachlorodiphenyl-1,1-cyclohexane, 4,4'"'"'-dihydroxy-3,3'"'"',5,5'"'"'-tetrachlorodiphenyl-2,2-propane, dihydroxydiphenyl-1,1'"'"'-diphenylmethane, 4,4'"'"'-dihydroxy-3,3'"'"'-dichlorodiphenyl-2,2-propane, difluoro-(1,1'"'"'-biphenyl)-4,4-diol, 3,3'"'"',5,5'"'"'-tetrafluoro-(1,1'"'"'-biphenyl)-2,2'"'"'-diol, 2,2'"'"'-bis-(4-hydroxyphenyl-1,3-perfluoropropane, 2,2-bis(4-hydroxy-2,3,5-trichlorophenyl)propane, 2,2-bis(3-hydroxyphenyl-1,3-perfluoropropane), and 2-bis(4-hydroxyphenyl-1,1'"'"',3,3'"'"'-chlorodifluoropropane).