Use of organic oxyimides as radical generators in plastics, method for generating radicals in plastics and use of said method

Patent metadata

Field	Value
Publication number	US-10364340-B2
Application number	US-201515511471-A
Country	US
Kind code	B2
Filing date	Sep 16, 2015
Priority date	Sep 18, 2014
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

The present invention relates to the use of phosphorus-containing organic oxyimides according to the general formula I described below as flame retardant for plastic materials, as radical generators in plastic materials and/or as stabilizers for plastic materials. The present invention relates in addition to a flame-retardant plastic material molding compound in which the previously described phosphorus-containing organic oxyimides are integrated, and also to a method for the production of the previously mentioned plastic material composition. Furthermore, the present invention relates to a molded part, a paint or a coating made of the previously mentioned flame-retardant plastic material composition.

First claim

The invention claimed is:

1. A method of incorporating a radical generator into a plastic material comprising incorporating into said plastic material an organic oxyimide having the structural element of formula I

wherein the radical generator is activated thermally or by irradiation,
wherein the activation is accomplished during shaping of the plastic material or shaping of a moulding compound comprising the plastic material,
wherein the thermal activation is accomplished at a temperature of 240° C. or more,
said method resulting in a modification of the plastic material, wherein the modification is increasing the molecular weight of the plastic material, branching or crosslinking of the plastic material, molecular weight decrease of the plastic material, influencing a molecular weight distribution of the plastic material, and/or grafting of an unsaturated monomer onto the plastic material.

2. The method according to claim 1 , wherein the oxyimide is selected from the group consisting of
a) oxyimides comprising at least one structural element of formula II

wherein R 1 is hydrogen or an optionally substituted alkyl-, cycloalkyl-, aryl-, heteroaryl- or acyl-radical, and
b) bridged oxyimides comprising at least one structural element of formula III,

wherein R 2 is an optionally substituted akylene-, cycloalkylene-, arylene-, heteroarylene- or bridging acyl-radical.

3. The method according to claim 2 , wherein R 2 is selected from the group consisting of
—(CH 2 ) n — with n=1 to 18, —CH(CH 3 )—, —C(CH 3 ) 2 —, —O—, —S—, —SO 2 —, —NHCO—, —CO—

wherein the cycloaliphatic or aromatic ring systems contained in the above groups is unsubstituted or substituted by one or more alkyl- and/or alkoxy-groups,
Q upon each occurrence, is the same or different and is selected from the group consisting of a chemical bond, —(CH 2 ) n — with n=1 to 18, —CH(CH 3 )—, —C(CH 3 ) 2 —, —O—, —S—, —SO 2 —, —NHCO—, —CO—, OC(O)—O— and
m is 0 or 1 to 18.

4. The method according to claim 1 , wherein the organic oxyimide has one of the following formulae,

wherein R 1 is hydrogen or an optionally substituted alkyl-, cycloalkyl-, aryl-, heteroaryl- or acyl-radical, and
R 2 is selected from the group consisting of
—(CH 2 ) n — with n=1 to 18, —CH(CH 3 )—, —C(CH 3 ) 2 —, —O—, —S—, —SO 2 —, —NHCO—, —CO—,

wherein the cycloaliphatic or aromatic ring systems contained in the above groups is unsubstituted or substituted by one or more alkyl- and/or alkoxy-groups,
Q upon each occurrence, is the same or different and is selected from the group consisting of a chemical bond, —(CH 2 ) n — with n=1 to 18, —CH(CH 3 )—, —C(CH 3 ) 2 , —O—, —S—, —SO 2 —, —NHCO—, —CO—, OC(O)—O— and
m is 0 or 1 to 18.

5. The method according to claim 2 , wherein R 1 =H, R 1 =alkyl or R 1 =acyl.

6. The method according to claim 1 , which further includes incorporating at least one chain transfer agent.

7. The method according to claim 1 , which further includes incorporating at least one multifunctional compound selected from the group consisting of
a) repeatedly unsaturated oligomers and polymers based on polybutadiene or polyisoprene,
b) di- and polyvinyl compounds,
c) di- and polyallyl compounds,
d) di- and polymaleimides,
e) di- and poly(meth)acrylesters of di- and polyalcohols, and
f) organofunctional silanes, and combinations thereof.

8. The method according to claim 1 , which further includes incorporating at least one nitroxyl radical.

9. The method according to claim 1 , which further includes incorporating at least one catalytic compound.

10. The method according to claim 1 , which includes incorporating at least one further radical former.

11. The method according to claim 10 , wherein the further radical former is selected from the group consisting of N-alkoxyamines, —C—C— radical formers, radical formers with azo groups (—N═N—), radical formers with hydrazine groups (—NH—HN—), radical formers with hydrazone groups (>C═N—NH—), radical formers with azine groups (>C═N—N═C<), radical formers with triazene groups (—N═N—N<), radical formers with disulfide- or polysulfide groups (—S—S—), radical formers with thiol groups (—S—H), thiuram sulfide, dithiocarbamates, mercaptobenzothiazole, and sulphenamides.

12. The method according to claim 11 , wherein the further radical former is selected from the group consisting of
a) N-alkoxyamines according to the structural formula

wherein
R 3 is hydrogen or an optionally substituted alkyl-, cycloalkyl-, aryl-, heteroaryl- or acyl-radical,
R 4 is an alkoxy-, aryloxy-, cycloalkoxy-, aralkoxy- or acyloxy-radical,
Z is hydrogen or an optionally substituted alkyl-, cycloalkyl-, aryl-, heteroaryl- or acyl-radical, or two Z radicals form a closed ring which is optionally substituted with an ester-, ether-, amine-, amide-, carboxy- or urethane-group,

b) azo compounds according to the structural formulae
R 5 —N═N—R 5

 or

wherein
R 5 is an alkyl-, cycloalkyl- or aryl-radical,
R 6 upon each occurrence, is the same or different and is a linear or branched alkyl-radical,
R 7 upon each occurrence, is the same or different and is hydrogen or a linear or branched alkyl-radical, and
R 8 upon each occurrence, is the same or different and is an alkyl-, alkoxy-, aryloxy-, cycloalkyloxy-, aralkoxy or acyloxy-radical,

c) dicumylenes according to the structural formula

wherein R 7 has the previously indicated meaning, and

d) polycumylenes according to the structural formula

wherein R 7 has the previously indicated meaning and 2<n<100.

13. The method according to claim 1 , wherein the plastic materials are thermoplastic, elastomeric or duroplastic polymers.

14. The method according to claim 13 , wherein the plastic materials are thermoplastic polymers.

15. The method according to claim 14 , wherein the thermoplastic polymers are selected from the group consisting of
a) polymers made of olefins or diolefins,
b) polystyrene, polymethylstyrene, polyvinyl naphthalene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene-propylene-styrene, styrene-isoprene, styrene-isoprene-styrene (S

Assignees

• Fraunhofer Ges Forschung

Inventors

• Pfaendner Rudolf
• Mazurowski Markus

Classifications

• C09D5/18

  Fireproof paints {including high temperature resistant paints} · CPC title

• C08K5/5353 Primary

  containing also nitrogen · CPC title

• C09K21/12

  containing phosphorus · CPC title

• C09K15/30

  containing heterocyclic ring with at least one nitrogen atom as ring member · CPC title

• C08K5/53

  bound to oxygen and to carbon only · CPC title