2,2,6,6-Tetramethyl-4-piperidyl carboxylic acid esters and amides of mono and poly alcohols, phenols and amines and synthetic polymer compositions stabilized thereby
申请人:ADEKA ARGUS CHEMICAL CO., Ltd.
公开号:EP0022997A1
公开(公告)日:1981-01-28
2,2,6,6-Tetramethyl-4-piperidyl carboxylic acid esters and amides of mono and poly alcohols, phenols and amines are provided, useful as stabilizers for organic polymeric materials, and having the general formula:
wherein:
R1, R2 and R3 are selected from the group consisting of hydrogen and alkyl having from one to about eighteen carbon atoms;
X is oxygen or imino >NH;
m is zero, 1 or 2;
n is zero, 1 or 2;
m + n is 1 or 2;
p is zero or 1;
q is 1 to 6;
is linked to carbon in place of one R2 or R, group; and
is selected from the group consisting of:
(a) OR5 where R5 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and hydroxy-, carboxy- and oxy-substituted such groups having from one to five OH or O groups; and 2,2,6,6-tetramethyl-4-piperidyl;
(b) OReO where Re is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and hydroxy-substituted such groups having one to four OH groups; Re alkylene, aryiene or cycloalkylene can include oxyether -0- and thioether -S- linking groups attached to alkylene, arylene or cycloalkylene groups as in polyoxyalkylene and polythioalkylene groups and polyoxyalkylene arylene groups having from one to about five oxy or thio groups and from two to about six alkylene groups having (c)
from two to about six carbon atoms; where R6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and hydroxy-substituted such groups having one to four OH groups; R6 alkylene, arylene or cycloalkylene can include oxyether -O- and thioether -S- linking groups attached to alkylene, arylene or cycloalkylene groups as in polyoxyalkylene and polythioalkylene groups and polyoxyalkylene arylene groups having from one to about five oxy or thio groups and from two to about six alkylene groups having from two to about six carbon atoms; R7 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and hydroxy-substituted such groups having from one to five OH groups; (d)
where R5 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and amino-substituted such groups having (e)
from one to five amino groups; where R6 is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and amino-substituted such groups having one to four amino groups; R7 is alkyl, aryl or cycloalkyl having one to twenty-four carbon atoms and amino-substituted such groups having one to five amino groups; (f)-NHNH2; -NHNH-; -NHNHCOCONHNH2; NHNHCOR7; -NHNHCOR6CONHNH2; -NHNHCOR6CONHNH-; -NHNHCOCONHNH-,; -NHR6NH2-; -NHR6NH-;
where Rs is alkylene, arylene or cycloalkylene having one to twenty-four carbon atoms and amino-substituted such groups having one to four amino groups; and such groups including oxyether and thioether linking groups as in (b) above, and R7 is as in (c) above.
本发明提供了 2,2,6,6-四甲基-4-哌啶基羧酸酯和一元醇和多元醇、酚和胺的酰胺,可用作有机聚合物材料的稳定剂,其通式为
其中
R1、R2 和 R3 选自氢和具有 1 至约 18 个碳原子的烷基组成的组;
X 是氧或亚胺 >NH;
m 为零、1 或 2
n 为零、1 或 2
m + n 为 1 或 2;
p 为 0 或 1
q 为 1 至 6;
与碳相连,代替一个 R2 或 R, 基团;以及
选自以下组成的组
(a) OR5,其中 R5 是具有 1 至 24 个碳原子的烷基、芳基或环烷基,以及具有 1 至 5 个 OH 或 O 基团的羟基、羧基和氧基取代的此类基团;以及 2,2,6,6-四甲基-4-哌啶基;
(b) OReO 其中 Re 为具有 1 至 24 个碳原子的亚烷基、芳基或环烷基,以及具有 1 至 4 个 OH 基团的羟基取代的此类基团;Re亚烷基、芳基或环烷基可包括连接到亚烷基、芳基或环烷基上的氧醚 -0- 和硫醚 -S- 连接基团,如聚氧亚烷基、聚硫亚烷基和聚氧亚烷基芳基中的氧醚 -0- 和硫醚 -S- 连接基团,这些基团具有 1 至 5 个氧基或硫代基团和 2 至 6 个亚烷基,这些亚烷基具有 (c)
R6是具有一至二十四个碳原子的亚烷基、芳基或环烷基,以及具有一至四个羟基的羟基取代的亚烷基、芳基或环烷基;R6 亚烷基、亚芳基或环烷基可包括连接到亚烷基、亚芳基或环烷基上的氧醚 -O- 和硫醚 -S- 连接基团,如聚氧亚烷基和聚硫亚烷基以及聚氧亚烷基亚芳基中的氧醚 -O- 和硫醚 -S- 连接基团,这些亚烷基、亚芳基或环烷基具有一至约五个氧或硫基和二至约六个亚烷基,这些亚烷基具有二至约六个碳原子;R7 是具有一至二十四个碳原子的烷基、芳基或环烷基,以及具有一至五个羟基的羟基取代的此类基团; (d)
其中 R5 是具有一至二十四个碳原子的烷基、芳基或环烷基和具有 (e)
R6 是具有 1 至 24 个碳原子的亚烷基、芳基或环烷基,以及具有 1 至 4 个氨基的氨基取代的此类基团;(f)-NHNH2; -NHNH-; -NHNHCOCONHNH2; NHNHCOR7; -NHNHCOR6CONHNH2; -NHNHCOR6CONHNH-; -NHNHCOCONHNH-,; -NHR6NH2-;-NHR6NH-;
其中 Rs 是具有一至二十四个碳原子的亚烷基、芳烯基或环烷基,以及具有一至四个氨基的氨基取代的此类基团;此类基团包括如上文(b)所述的氧醚和硫醚连接基团,R7 如上文(c)所述。