Dimeric light stabilizers for polyolefines and polyolefine...

Details Dimeric light stabilizers for polyolefines and polyolefine... Dimeric light stabilizers for polyolefines and polyolefine...

2000-11-27

2002-12-17

Szekely, Peter (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

C568S332000, C568S333000, C556S436000

Reexamination Certificate

active

06495622

ABSTRACT:

The invention relates to novel compositions comprising a polyolefin or polyolefin copolymer, and a dimeric 2-hydroxybenzophenone as stabilizer against damage by light, oxygen and/or heat; and further to novel compounds of the 2-hydroxybenzophenone class useful as stabilizers for organic material, and a corresponding process of stabilizing.
A considerable number of organic compounds containing a group 2-hydroxybenzophenone are known to be efficient light stabilizers for protecting organic materials against deleterious effects of (ultraviolet) light, oxygen and heat. Some dimeric benzophenones known from U.S. Pat. No. 3,580,927 have been recommended for the stabilization of certain polyesters.
Some compounds have now been found showing surprisingly good properties for the stabilization of polyolefines or polyolefin copolymers against harmful effects of actinic light, oxygen and heat.
Thus, present invention pertains to a composition comprising
A) a polyolefin or polyolefin copolymer, and
B) as stabilizer against damage by light, oxygen and/or heat, a compound of the formula I
wherein
R
1
is O or O—X—O;
R
2
, R
3
, R
4
and R
5
independently are hydrogen, halogen, C
1
-C
8
alkyl, C
1
-C
8
alkoxy, SR
10
,
SO
2
R
10
, phenyl, CF
3
, COOR
11
; and wherein R
2
and R
3
also may be OH;
R
6
and R
7
are H or C
1
-C
8
alkyl;
R
8
and R
9
are H, C
1
-C
8
alkyl or allyl;
R
10
is phenyl or C
1
-C
12
alkyl;
R
11
is C
1
-C
8
alkyl; C
3
-C
50
alkylene interrupted by one or more O; cyclohexyl; benzyl; allyl;
X is C
2
-C
18
alkylene; C
3
-C
12
hydroxyalkylene; or a group selected from those of the formulae
where D and D′ independently are a direct bond or C
1
-C
3
alkylene; and Y is O, S, SO
2
, or C
1
-C
3
alkylene.
Alkylene, cycloalkylene or alkenylene residues may be bonded on different carbon atoms or on the same carbon atom thus embracing alkylidene, cycloalkylidene and alkenylidene, respectively.
All residues, where appropriate, may be straight chain or branched unless otherwise indicated. Alkyl or alkylene interrupted by a spacer such as oxygen may be interrupted by one or more spacers as long as no linkages of the type O—O etc. occur.
Halogen is F, Cl, Br or l; preferably chloro or fluoro, especially chloro.
The compounds of formula I can be pure or mixtures of compounds.
R
1
R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, as alkyl are, within the definitions given, for example methyl, ethyl, propyl such as n- or isopropyl, butyl such as n-, iso-, sec- and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl. Alkoxy is O-alkyl. X, D and Y as alkylene are, within the definitions given, for example methylene, 1,2-ethylene, 1,1-ethylene, 1,3-propylene, 1,2-propylene, 1,1-propylene, 2,2-propylene, 1,4-butylene, 1,3-butylene, 1,2-butylene, 1,1-butylene, 2,2-butylene, 2,3-butylene, or —C
5
H
10
—, —C
6
H
12
—, C
7
H
14
, —C
8
H
16
—, —C
9
H
18
—, —C
10
H
20
—, —C
11
H
22
—, —C
12
H
24
—, —C
13
H
26
—, —C
14
H
28
—, —C
15
H
30
—, —C
16
H
32
—, —C
17
H
34
—, —C
8
H
36
—. D and Y are especially preferred as methylene. X as hydroxyalkylene is alkylene substituted by one or more OH and includes, for example, groups of the formulae CH
2
CH(OH)CH
2
, CH
2
—C(CH
2
OH)
2
—CH
2
.
Preferred in the compositions of the invention are compounds corresponding to the formula
wherein
R
1
is O or O—X—O;
R
2
and R
3
are hydrogen, Cl, C
1
-C
8
alkyl, C
1
-C
4
alkoxy, OH;
R
4
and R
5
are hydrogen, Cl, F, C
1
-C
8
alkyl, C
1
-C
4
alkoxy, SR
10
, SO
2
R
10
, phenyl, CF
3
, COOR
11
;
X is C
2
-C
12
alkylene; phenylene, or a group selected from those of the formulae
where D and D′ independently are a direct bond or are methylene; and
Y is O, S, SO
2
, or C
1
-C
3
alkylene.
More preferred is a compound of the formula I wherein
R
1
is O or O—X—O;
R
2
and R
3
are hydrogen, Cl, C
1
-C
8
alkyl, C
1
-C
4
alkoxy, OH;
R
4
and R
5
are hydrogen, Cl, C
1
-C
8
alkyl, C
11
-C
4
alkoxy, SR
10
, SO
2
R
10
, phenyl,
X is C
2
-C
12
alkylene; cyclohexylene, or a group selected from those of the formulae
where Y is O, S, SO
2
, methylene or —C(CH
3
)
2
—.
Most preferred is a compound of the formula I wherein
R
1
is O—X—O,
R
2
and R
3
are hydrogen, Cl;
R
4
and R
5
are hydrogen, Cl, C
1
-C
8
alkyl, C
1
-C
4
alkoxy, SR
10
, SO
2
R
10
, phenyl, CF
3
;
R
6
, R
7
, R
8
and R
9
are each H,
X is C
2
-C
12
alkylene; cyclohexylene, or a group selected from those of the formulae
where Y is methylene or —C(CH
3
)
2
—; especially wherein
R
2
and R
3
are hydrogen;
R
4
and R
5
are hydrogen or Cl;
R
6
, R
7
, R
8
and R
9
each are hydrogen.
X is most preferred as C
8
-C
18
alkylene, usually unbranched; especially preferred is X selected from the group consisting of (CH
2
)
8
; (CH
2
)
10
; (CH
2
)
12
; (CH
2
)
18
.
Of special importance as component A are polyolefines or polyolefin copolymers as described in sections 1-3 below, especially in the form of films, ribbons, tapes, fibers or fabrics, e.g. for agricultural or packaging uses. Examples for specific uses include:
Polypropylene non-woven fabric
Polyolefin films with an antifog
for agricultural applications,
agent
e.g. shade cloth
Polyolefin films with an antistatic
Polyolefin films with IR thermal
agent
fillers such as hydrotalcites,
e.g. DHT4A
Polypropylene tape or slit film
Polypropylene non-woven fabrics
Polyethylene non-woven fabrics
Polyethylene greenhouse films,
optionally containing hindered
amine light stabilizers
and/or hydrotalcites
Flame-resistant polypropylene fiber
Flame-resistant polethylene film
Polyolefin foodpackaging film
The polyolefin or polyoiefin copolymer of present component A is, for example, selected from the following polymers:
1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for instance of cyclopentene or norbornene, polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultrahigh molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE).
Polyolefins, i.e. the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:
a) radical polymerisation (normally under high pressure and at elevated temperature).
b) catalytic polymerisation using a catalyst that normally contains one or more than one metal of groups IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either &pgr;- or &tgr;-coordinated. These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium. The catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups Ia, Ia and/or IIIa of the Periodic Table. The activators may be modified conveniently with further ester, ether, amine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).
2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP/HDPE, PP/LDPE) and mixtures of different types of polyethylene (for example LDPE/HDPE).
3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, for e

Affiliated with

Also associated with

Rating

Dimeric light stabilizers for polyolefines and polyolefine... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Dimeric light stabilizers for polyolefines and polyolefine..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Dimeric light stabilizers for polyolefines and polyolefine... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2941628