Phosphorus-containing flameproofing agents for epoxy resin materials

• US 5,506,313 A
• Filed: 09/07/1994
• Issued: 04/09/1996
• Est. Priority Date: 09/09/1993
• Status: Expired due to Fees

• Current Assignee: Huntsman Advanced Materials Americas, Inc.
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Vanoli, Ennio, Flury, Peter, Scharf, Wolfgang, Mayer, Carl W.
• Primary Examiner(s): KRASS, FREDERICK F
• Application Number:
  US08/301,468
• Time in Patent Office: 580 Days
• Field of Search: 558/162, 549/219, 528/99, 525/523, 525/525
• US Class Current: 525/523
• CPC Class Codes: C07F 9/12 with hydroxyaryl compounds
• CPC Class Codes: C07F 9/65502 the oxygen atom being part of a three-membered ring
• CPC Class Codes: C08G 59/066 with chain extension or advancing agents
• CPC Class Codes: C08G 59/304 containing phosphorus
• CPC Class Codes: C08G 59/3254 containing atoms other than carbon, hydrogen, oxygen or nitrogen
• CPC Class Codes: H05K 1/0326 containing O

Abstract

The invention relates to compounds of the formula (1) ##STR1## in which m is 0 or 1,

R is a hydrogen atom or a group of formula ##STR2## T is either an (m+2)-valent aromatic group or a bisphenylene group, [Z] is a group of on average 1 to 10 structural units of the formula (3)

--Q--T(OR).sub.1+m-r (EB).sub.r                            (3),

in which

Q is a group of the formula (4) ##STR3## in which R⁰ is a phenyl radical substituted in a particular manner and

R¹ and

R² are C₁ -C₄ alkyl, and in which, furthermore,

EB symbolizes a free valency of the group T,

r has one of the values 0, 1 or 1+m

and the structural units of the formula (3) are linked via their free valencies to the group [Z] such that the groups Q in each case alternate with groups T and the group [Z] overall is monovalent. As excellent flameproofing agents which are reactive towards epoxy compounds, the compounds are a useful formulation component for epoxy resin compositions.

Claims

1. A compound of the formula (1) ##STR22## in which m is 0 or 1,

R is a hydrogen atom or a group of formula ##STR23## T is either an (m+2)-valent aromatic group having 6 to 14 ring carbon atoms or an (m+2)-valent group which is derived, by removal of (m+2) aromatic hydrogen atoms, from a compound of the formula (2) ##STR24## in which Y is a chemical structural element selected from the group consisting of a single bond and the groups of the formula --O--, --S--, >

SO₂, >

C═

O and ##STR25## in which R⁶ and

R⁷ independently of one another in each case are a hydrogen atom or a methyl group, and

[Z] is a group which comprises on average 1 to 10 structural units which are structural units of the formula (3)

space="preserve" listing-type="equation">--Q--T(OR).sub.1+m-r (EB).sub.r (

     3),

in which

Q is a group of the formula (4) ##STR26## in which R⁰ is a radical of the formula (5) ##STR27## R¹ and R² and

R³ independently of one another in each case are a C₁ -C₄ alkyl group,

R⁴ is a hydrogen atom or a C₁ -C₄ alkyl group and

R⁵ is a hydrogen, bromine or chlorine atom, a hydroxyl group or a group of formula ##STR28## and in formula (3) furthermore T has the same meaning as in formula 1,

EB symbolizes a free valency of the group T and

r has one of the values 0, 1 or 1+m,

and in which the structural units of the formula (3) are linked via their free valencies to the group [Z] such that the groups Q in each case alternate with groups T and the group [Z] overall is monovalent,

with the proviso that [Z] is a group --[Q--T]_k --OR in which k is a value from 2 to 5 if m is 0.

2. A compound according to claim 1, in which

m is 0.

3. A compound according to claim 2, in which

T is selected from the group consisting of 1,3-phenylene, 1,4-phenylene, 1,5-naphthylene and 2,2'"'"'-bis(4-phenylene)-propane.

4. A compound according to claim 1, in which

m is 1.

5. A compound according to claim 1, in which

m is 1 and

T is a group of the formula ##STR29##

6. A compound according to claim 1, in which

[Z] is composed of 2 to 5 structural elements of the formula (3).

7. A compound according to claim 1, in which

R⁵ is a hydrogen atom, a hydroxyl group or a group of formula ##STR30##

8. A compound according to claim 7, in which

R⁵ is a hydrogen atom.

9. A compound of the formula (1) according to claim 1, wherein R is a group of the formula ##STR31##