JP2013518959A5

JP2013518959A5 -

Info

Publication number: JP2013518959A5
Application number: JP2012551623A
Authority: JP
Filing date: 2011-02-03
Publication date: 2014-03-20

Claims

One or more formulas (I) for a given material
S = PR ¹ R ² R ³ (I)

[In the formula (I),
R ¹ and R ² may be the same or different and are C ₁ -C ₁₂ -alkyl, C ₃ -C ₈ -cycloalkyl (even if unsubstituted, one or more C ₁ -C ₄ -alkyl groups are which may have as a _{substituent),} C 2 _{-C 12} - _alkenyl, C 2 _{-C 12} - _alkynyl, C 6 _{-C 10} - aryl or _C 6 _{-C 10,} - aryl _-C 1 -C ₄ - Is alkyl;
R ³ is H, SH, SR ⁴ , OH, OR ⁵ or — (Y ¹ ) _n — [P (═X ¹ ) R ⁶ — (Y ² ) _n ] _m —P (= X ² ) R ⁷ R ⁸ groups;
Or two groups of R ¹ , R ² and R ³ form a ring system with a phosphorus atom bonded thereto;
X ¹ and X ² are the same or different and are O or S;
Y ¹ and Y ² are the same or different and are O or S;
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ are the same or different and independently of each other,
C ₁ -C ₁₂ -alkyl, C ₃ -C ₈ -cycloalkyl (which may be unsubstituted or may have one or more C ₁ -C ₄ -alkyl groups as substituents), C _2- C ₁₂ -alkenyl, C ₂ -C ₁₂ -alkynyl, C ₆ -C ₁₀ -aryl, or C ₆ -C ₁₀ -aryl-C ₁ -C ₄ -alkyl;
When Y ¹ and Y ² are O, n is 1,
When Y ¹ and Y ² are each S, n is 1, 2, 3, 4, 5, 6, 7, or 8;
m is an integer from 0 to 100]
A method for making a material flame-retardant, comprising a step of adding a phosphine sulfide derivative .

The method according to claim 1, wherein in formula (I):
R ¹ and R ² are the same or different and are C ₁ -C ₈ -alkyl, cyclohexyl, phenyl or benzyl;
R ³ is H, SH, SR ⁴ or — (Y ¹ ) _n — [P (═X ¹ ) R ⁶ — (Y ² ) _n ] _m —P (═X ² ) R ⁷ R ⁸ ;
Or two groups R ¹ and R ² and R ^3, forms a ring Jomoto with phosphorus atoms bonded thereto;
X ¹ and X ² are S;
Y ¹ and Y ² are the same or different and are O or S;
R ⁴ , R ⁶ , R ⁷ , R ⁸ are the same or different and are independently of each other C ₁ -C ₈ -alkyl, cyclohexyl, phenyl or benzyl;
When Y ¹ and Y ² are each O, n is 1,
When Y ² is S, n is 1 or 2,
m is an integer of 0-10 .

The method according to claim 1 or 2, wherein in formula (I):
R ¹ and R ² are phenyl;
R ³ is H, SH, S-benzyl, or (Y ¹ ) _n —P (═S) R ⁷ R ⁸ group;
Y ¹ is the same or different and is O or S;
R ⁷ and R ⁸ are phenyl;
When Y ¹ is O, n is 1,
A method wherein n is 1 or 2 when Y ¹ is S.

4. The method according to any one of claims 1 to 3, wherein the compound of formula (I) is in the following group:
^{^{S = PR 1 R 2 -H (}} Ia);
^{^{S = PR 1 R 2 -SH (}} Ib);
S ⁼ PR ¹ R 2 -S- benzyl (Ic);
^{^{^{S = PR 1 R 2 -S-}}} P (= S) R 7 R 8 (Ida);
^{^{S = PR 1 R 2 -S-}} S-P (= S) R 7 R 8 (Idb);
An ^{^{S = PR 1 R 2 -O-}} P (= S) R 7 R 8 (Idc),
(The definitions of these symbols are the same as those described in formula (I) according to any one of claims 1 to 3).
Method selected from .

The compound of formula (I) is obtained from diphenyldithiophosphinic acid and diphenylphosphine sulfide, benzylphosphinodithioate, diphenylthiophosphinic acid thioanhydride, bis (diphenylphosphinothioyl) disulfide, diphenylthiophosphinic acid anhydride. The method according to any one of claims 1 to 4, which is selected.

The R ³ group in formula (I) is SH, SR ⁴ , OH, OR ⁵ , or — (Y ¹ ) _n — [P (═X ¹ ) R ⁶ — (Y ² ) _n ] _m —P (= X ²⁾ the method according to claim 1 or 2 is ^R 7 ^{R 8} group.

R ³ is SH, SR ⁴ , or — (Y ¹ ) _n — [P (═X ¹ ) R ⁶ — (Y ² ) _n ] _m —P (═X ² ) R ⁷ R ⁸ (where Y The method according to claim 6, wherein ¹ = S).

R ³ is SH, or — (Y ¹ ) _n — [P (═X ¹ ) R ⁶ — (Y ² ) _n ] _m —P (═X ² ) R ⁷ R ⁸ (where Y ¹ = S 8. The method of claim 7, wherein

The method according to any one of claims 1 to 8, wherein one compound of the formula (I) is used.

The method according to any one of claims 1 to 8, wherein at least two compounds of the formula (I) are used.

11. A method according to any one of the preceding claims, wherein the compound of formula (I) is added to a mixture of one or more other flame retardants and one or more synergists, respectively.

The method according to claim 1, added pressure to the flame retardant according to any one of claims 1 to 11 in foamed or non-foamed polymer over.

A polymer composition comprising one or more polymers and the flame retardant according to any one of claims 1-11.

14. The polymer composition according to claim 13, comprising 0.1 to 25 parts by weight (based on 100 parts by weight of polymer) flame retardant.

The polymer composition according to claim 13 or 14, which is halogen-free.

The polymer composition according to any one of claims 13 to 15, comprising a styrene polymer.

The polymer composition according to any one of claims 13 to 16, wherein the polymer is a polymer foam.

The polymer composition of claim 16 in the form of an expandable styrene polymer (EPS).

a) other additions of an organic blowing agent and optionally one or more compounds of formula (I) according to any one of claims 1 to 11, at a temperature of at least 150 ° C by means of a static mixer or a dynamic mixer. Mixing agents and / or auxiliaries for introduction into the styrene polymer melt;
b) cooling the blowing agent-containing styrene polymer melt to a temperature of at least 120 ° C;
c) discharging through a perforated die plate having a hole diameter of 1.5 mm or less at the die outlet;
The process for producing an expandable styrene polymer (EPS) according to claim 18, comprising: d) granulating the foam-containing melt immediately after the die plate under a pressure in the range of 1 to 20 bar in water.

a) polymerizing one or more styrene monomers in suspension;
b) before, during and / or after polymerization, adding one or more compounds of formula (I) according to any one of claims 1 to 11 and, if necessary, other additives and / or auxiliaries And a process of
c) adding an organic blowing agent before, during and / or after polymerization;
19. A process for producing an expandable styrene polymer (EPS) according to claim 18, comprising d) separating expandable styrene polymer particles containing one or more compounds of formula (I) from the suspension.

The polymer composition of claim 17 in the form of an extruded styrene polymer foam (XPS).

a) heating a polymer component P containing at least one styrene polymer to form a polymer melt;
b) introducing a blowing agent component T into the polymer melt to form a foamable melt;
c) extruding the foamable melt into a relatively low pressure region while foaming to obtain an extruded foam;
d) at least one step of steps a) and / or b) comprising adding at least one compound of formula (I) according to claim 1 and, if appropriate, other auxiliaries and additive materials. A method for producing an extruded foam of the styrene polymer (XPS) according to claim 21.

An insulating material comprising the halogen-free polymer composition according to claim 21 or the halogen-free polymer composition according to claim 18 in foamed form.