Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Compound of indeterminate structure – prepared by reacting a...
Reexamination Certificate
2000-08-21
2002-09-10
Howard, Jacqueline V. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Compound of indeterminate structure, prepared by reacting a...
C508S222000, C508S272000, C508S276000, C508S284000, C508S322000, C252S404000, C252S405000, C252S406000, C044S330000, C554S002000
Reexamination Certificate
active
06448208
ABSTRACT:
The present invention relates to novel liquid polyfunctional additives of low volatility, to compositions comprising an organic material, preferably a fuel or lubricant, or a polymer, and the said additives, and to the use thereof and the method of stabilizing organic materials against oxidative, thermal or light-induced degradation, and for reducing friction.
The stabilization, especially that of lubricants or plastics, with antioxidants from the series of the sterically hindered phenols or their reaction products with other compounds is known, for example, from U.S. Pat. Nos. 3,839,278, 4,032,562, 4,058,502, 4,093,587, 4,132,702, 5,478,875 and EP-A-0 644 195.
WO 91/13134 describes a method of improving the solubility of antioxidants in a second medium.
U.S. Pat. No. 5,380,890 discloses stabilizer mixtures in which the antioxidant active group amounts only to up to 20 per cent by weight. Such stabilizer mixtures, however, in some cases have the feature that they crystallize out after 2 to 3 weeks at room temperature and are therefore no longer flowable. There is therefore a need for stabilizer mixtures having a higher proportion of antioxidant active group and a better stability on storage, so that the product is still pumpable in the liquid state even after weeks.
There is likewise a search for compounds which combine their stabilizing properties with a friction-reducing effect. This additional property is achieved by means of free aliphatic OH groups, which bind the compound to the metallic (for example) surface to be protected and so position themselves between the surfaces at risk of frictional wear.
The present invention relates to a product obtainable by reacting components a), b), c) and, if desired, d), where component a) is a compound of the formula I or a mixture of compounds of the formula I component b) is a compound of the formula II or a mixture of compounds of the formula II, component c) is a component of the formula IIIa and/or of the formula IIIb or a mixture of compounds of the formula IIIa and/or IIIb, and component d) is a compound of the formula IV or a mixture of compounds of the formula IV,
where in the compound of the formula I
a is the integer 1, 2, 3, 4 or 6, and
if a is 1
R
1
is C
4
-C
30
alkyl or —CH
2
CH
2
—T—(CH
2
CH
2
O)
b
R
2
, and
b is an integer from the range from 0 to 30, and
T is oxygen, sulfur or
where
R
2
is C
1
-C
18
or
and
R
3
is hydrogen or C
1
-C
18
alkyl, and
c is an integer from the range from 0 to 3, or
if a is 2
R
1
is —C
d
H
2d
—, —CH
2
—CH═CH—CH
2
—, —CH
2
—C═C—CH
2
—,
—CH
2
CH
2
—T—(CH
2
CH
2
O)
b
—CH
2
CH
2
— or
where b and T are as defined above, and
d and e are an integer from the range from 2 to 6, and
R
4
and R
5
independently of one another are hydrogen, C
1
-C
18
alkyl or phenyl, or
if a is 3
R
1
is C
3
-C
10
alkanetriyl or
and
R
6
is hydrogen or methyl, or
if a is 4
R
1
is C
4
-C
10
alkanetetrayl,
or —(CH
2
CH
2
—S)
2
CH—CH(S—CH
2
CH
2
)
2
— or
if a is 6
R
1
is
and in the compound of the formula II
R
7
is hydrogen, methyl or tert-butyl, and
R
8
is hydrogen or C
1
-C
30
alkyl, and
Q is —CH
2
CH
2
—,
—CH
2
—S—C
f
H
2f
— or
where
f is 1 or2, and in the compound of the formula IIIa and IIIb
G is chlorine, bromine or —OR
10
,
R
9
is hydrogen, C
1
-C
30
alkyl, C
4
-C
30
alkenyl, phenyl, C
7
-C
9
phenylalkyl, C
5
-C
12
cycloalkyl, C
8
-C
22
hydroxyalkyl, C
8
-C
22
hydroxyalkenyl,
R
10
is hydrogen, C
1
-C
18
alkyl, C
8
-C
30
alkenyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl,
g is 7 or 8,
h is an integer from the range from 2 to 8,
x is 3 or 4, and
if x is 3
R
11
is C
3
-C
18
alkanetriyl or C
6
-C
8
cycloalkanetriyl, and
if x is 4
R
11
is C
4
-C
18
alkanetetrayl or C
6
-C
8
cycloalkanetetrayl, and in the compound of the formula IV
L is sulfur, R
12
—SH,
C
12
-C
30
alkane or
where
R
12
is C
1
-C
18
alkyl, C
7
-C
24
phenylalkyl, phenyl, C
7
-C
24
alkylphenyl, or unsubstituted or C
1
-C
4
-alkyl-substituted C
5
-C
12
cycloalkyl; and
R
13
and R
14
independently of one another are C
1
-C
18
alkyl, or unsubstituted or C
1
-C
18
alkyl-substituted phenyl, and
R
15
is C
8
-C
30
alkyl.
The liquid and low-volatility products of the present invention are notable for very good stabilization of organic materials, such as fuels, polymers or oils, against oxidative, thermal and light-induced degradation.
Alkyl of up to 30 carbon atoms is a branched or unbranched radical such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, docosyl or pentacosyl. One of the preferred definitions of R
1
is for example C
8
-C
18
alkyl, of R
4
and R
5
C
1
-C
13
alkyl, of R
7
tert-butyl, of R
8
hydrogen or methyl, of R
9
C
7
-C
20
alkyl and of R
13
and R
14
isopropyl or isooctyl.
Cycloalkyl of up to 12 carbon atoms is for example cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl or cyclododecyl. One of the preferred definitions of R
9
, R
10
and R
12
is C
5
-C
7
cycloalkyl. Cyclohexyl is particularly preferred.
Unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
12
cycloalkyl is for example cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, tert-butylcyclohexyl, cycloheptyl or cyclooctyl. C
5
-C
8
cycloalkyl is preferred, especially cyclohexyl and tert-butylcyclohexyl.
Alkenyl of up to 30 carbon atoms is for example vinyl, propenyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methylbut-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, oleyl, n-octadec-2-enyl or n-octadec-4-enyl. One of the preferred definitions of R
9
is for example C
12
-C
24
alkenyl.
Hydroxyl-substituted C
8
-C
22
alkyl is a branched or unbranched radical containing preferably 1 to 3, especially 1 or 2, OH groups, such as 8-hydroxyoctyl, 7-hydroxyoctyl, 6-hydroxyoctyl, 5-hydroxyoctyl, 4-hydroxyoctyl, 3-hydroxyoctyl, 2-hydroxyoctyl, 9-hydroxynonyl, 10-hydroxydecyl, 11-hydroxyundecyl, 12-hydroxydodecyl, 13-hydroxytridecyl, 14-hydroxytetradecyl, 15-hydroxypentadecyl, 16-hydroxyhexadecyl, 17-hydroxyheptadecyl, 18-hydroxyoctadecyl, 20-hydroxyeicosyl or 22-hydroxydocosyl. A preferred definition of R
9
is hydroxyl-substituted C
8
-C
20
alkyl, especially hydroxyl-substituted C
8
-C
12
alkyl.
Phenylalkyl of 7 to 9 carbon atoms is for example benzyl, &agr;-methylbenzyl, &agr;,&agr;-dimethylbenzyl or 2-phenylethyl. Benzyl is preferred.
C
1
-C
18
alkyl-substituted phenyl, which contains preferably 1 to 3, especially 1 or 2, alkyl groups, is for example o-, m- or p-methylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2-methyl-6-ethylphenyl, 4-tert-butylphenyl, 2-ethylphenyl, 2,6-diethylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl or dodecylphenyl. C
1
-C
12
alkyl-substituted phenyl is preferred, especially C
4
-C
8
alkyl-substituted phenyl.
Alkanetriyl of 3 to 18 carbon atoms is for example
Glyceryl is preferred.
Alkanetetrayl of 4 to 18 carbon atoms is for example
Pentaerythrityl is preferred.
The reaction of the four components a), b), c) and d) with one another to form the products of the present invention can take place in any desired sequence.
Preferably, the four components a), b), c) and d) are introduced initially and reacted simultaneously.
Alternatively, component d) can be added to reaction mixtures a) and b), b) and c) or a) and c), and the missing fourth component can then be reacted.
A particularly preferred embodiment is the addition of the component d) after the reaction of the th
Allenbach Stephan
Dubs Paul
Evans Samuel
Martin Roger
Ribeaud Marc
Ciba Specialty Chemicals Corporation
Howard Jacqueline V.
Mansfield Kevin T.
Stevenson Tyler A.
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