IP Library Granted Patent US 12,617,886
Granted Patent B2
US 12,617,886 · App. 17/438,133 · Granted May 5, 2026

Liquid composition comprising a wax compound, its process of polymerization, use and material or composition obtained following polymerization of composition

Inventor: Pierre Gerard (Lacq, FR)
Assignee: ARKEMA FRANCE
C08F265/06C08J5/249C08L91/06D06M15/263
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Quick Facts
Patent No.
US 12,617,886
App. No.
17/438,133
Granted
May 5, 2026
Kind
B2
Abstract

A liquid composition including a monomer, a (meth)acrylic polymer and a wax compound. The liquid composition can be used as a syrup and especially as a syrup for impregnation of fibres or fibrous material. Also, a thermoplastic material obtained after polymerization of the liquid composition. Also, a process for manufacturing such a liquid composition. Also, a process for impregnating a fibrous substrate of long or continuous fibres with such a liquid composition. Also, a fibrous substrate impregnated with such a liquid composition which is useful for manufacturing composite parts. Also, a process for manufacturing mechanical parts or structural elements made of composite material and mechanical parts or structural elements made of composite material obtained via a process using such a liquid composition.

Claims (37)

1 . A liquid composition LC1 comprising,

a) a (meth)acrylic polymer (P1) having a weight-average molecular mass greater than 100,000 g/mol and comprising at least 90% by weight of methyl methacrylate,

b) a (meth)acrylic monomer (M1), wherein at least 80% by weight of the (meth)acrylic monomer (M1) is methyl methacrylate, and

c) between 0.45 phr and 1.4 phr relative to the sum of (meth)acrylic monomer (M1) and (meth)acrylic polymer (P1) of a wax compound (W) having a congealing point below 60° C.,

said liquid composition having a dynamic viscosity of between 25 mPa*s and 10,000 mPa*s at 25° C.,

wherein the (meth)acrylic polymer (P1) is present in a proportion not more than 30% by weight relative to the total weight of (meth)acrylic monomer (M1) and (meth)acrylic polymer (P1), and

wherein less than 5 wt % of the (meth)acrylic monomer (M1) evaporates at 23° C. for a duration of 20 minutes.

2 . The liquid composition LC1 as claimed in claim 1 , wherein the quantity of the wax compound (W) in the composition is between 0.5 phr and 1.3 phr relative to the sum of (meth)acrylic monomer (M1) and (meth)acrylic polymer (P1).

3 . The liquid composition LC1 according to claim 1 , wherein the density of the wax compound (W) is less than the density of the (meth)acrylic monomer (M1) and (meth)acrylic polymer (P1) together.

4 . The liquid composition LC1 according to claim 1 , wherein the density of the wax compound (W) is less than 1.1 g/cm 3 .

5 . The liquid composition LC1 according to claim 1 , wherein the density of the wax compound (W) is between 0.7 g/cm 3 and 1.1 g/cm 3 .

6 . The liquid composition LC1 according to claim 1 , wherein the liquid composition comprises additionally d) an initiator (Ini).

7 . The liquid composition LC1 according to claim 6 , wherein quantity the initiator (Ini) in the composition is between 0.75 phr and 8 phr relative to the sum of (meth)acrylic monomer (M1) and (meth)acrylic polymer (P1).

8 . The liquid composition LC1 according to claim 6 , wherein the initiator (Ini) is chosen from diisobutyryl peroxide, cumyl peroxyneodecanoate, di(3-methoxybutyl) peroxydicarbonate, 1,1,3,3-Tetramethylbutyl peroxyneodecanoate, cumyl peroxyneoheptanoate, di-n-propyl peroxydicarbonate, tert-amyl peroxyneodecanoate, di-sec-butyl peroxydicarbonate, diisopropyl peroxydicarbonate, di(4-tert-butylcyclohexyl) peroxydicarbonate, di-(2-ethylhexyl)-peroxydicarbonate, tert-amyl peroxyneodecanoate, tert-butyl peroxyneodecanoate, di-n-butyl peroxydicarbonate, dicetyl peroxydicarbonate, dimyristyl peroxydicarbonate, 1,1,3,3-tetramethylbutylperoxypivalate, tert-butyl peroxyneoheptanoate, tert-amyl peroxypivalate, tert-butyl peroxypivalate, di-(3,5,5-trimethylhexanoyl)-peroxide, dilauroyl peroxide, didecanoyl peroxide, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)-hexane, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, tert-amyl peroxy-2-ethylhexanoate, dibenzoyl peroxide, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxydiethylacetate, tert-butyl peroxyisobutyrate, 1,1-di-(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-di(tert-amylperoxy) cyclohexane, 1,1-di-(tert-butylperoxy)-cyclohexane, tert-amyl peroxy-2-ethylhexylcarbonate, tert-amyl peroxyacetate, tert-butyl peroxy-3,5,5-trimethylhexanoate, 2,2-di-(tert-butylperoxy)-butane, tert-butyl peroxyisopropylcarbonate, tert-butyl peroxy-2-ethylhexylcarbonate, tert-amyl peroxybenzoate, tert-butyl peroxyacetate, butyl 4,4-di(tert-butylperoxy)valerate, tert-butyl peroxybenzoate, di-tert-amylperoxide, dicumyl peroxide, di-(2-tert-butyl-peroxyisopropyl)-benzene, 2,5-dimethyl-2,5-di-(tert-butylperoxy)-hexane, tert-butylcumyl peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy) hexyne-3, di-tert-butyl peroxide, 3,6,9-triethyl-3,6,9-trimethyl-1,4,7-triperoxonane, 2,2′-azobisisobutyronitrile (AIBN), 2,2′-azodi-(2-methylbutyronitrile), azobisisobutyramide, 2,2′-azobis (2,4-dimethylvaleronitrile), 1,1′-Azodi(hexahydrobenzonitrile), or 4,4′-azobis (4-cyanopentanoic) and mixtures thereof.

9 . The liquid composition LC1 according to claim 1 , wherein the wax compound (W) has a congealing point is between 15° C. and 60° C.

10 . The liquid composition LC1 according to claim 1 , wherein the liquid composition LC1 comprises a monomer (M2) between 0.01 and 10 phr by weight relative to the sum of (meth)acrylic monomer (M1) and (meth)acrylic polymer (P1), said (meth)acrylic monomer (M2) comprises at least two (meth)acrylic functions.

11 . The liquid composition LC1 according to claim 1 , wherein the (meth)acrylic monomer(s) (M1) in the liquid composition LC1 or (meth)acrylic syrup are present in proportions of between 40% and 90% by weight of the composition comprising (meth)acrylic monomer(s) (M1) and (meth)acrylic polymer (P1).

12 . Process for preparing the liquid composition LC1 according to claim 1 , said process comprising the following steps:

i) preparing a mixture of (meth)acrylic polymer (P1) and (meth)acrylic monomer (M1);

ii) adding a wax compound (W) to the mixture prepared in previous step.

13 . The process according to claim 12 , wherein the (meth)acrylic polymer (P1) in the liquid composition LC1 or (meth)acrylic syrup is present in proportions of between 15% and 35% by weight and the (meth)acrylic monomer (M1) in the liquid composition LC1 or (meth)acrylic syrup is present in proportions of between 65% and 85% by weight of the composition comprising (meth)acrylic monomer (M1) and (meth)acrylic polymer (P1).

14 . The process according to claim 12 , wherein an initiator (Ini) is added to the the liquid composition LC1.

15 . The process according to claim 12 , wherein the in that the wax compound (W) has a congealing point is between 25° C. and 60° C.

16 . Process for manufacturing thermoplastic parts by a process comprising the following steps:

i) preparing a liquid mixture of (meth)acrylic polymer (P1) and (meth)acrylic monomer (M1)

ii) adding a wax compound (W) to the mixture prepared in previous step,

iii) putting the liquid (meth)acrylic composition prepared in i) and ii) in means for polymerization, said composition comprises additionally:

d) a initiator (Ini);

said liquid (meth)acrylic syrup having a dynamic viscosity of between 10 mPa*s and 10 000 mPa*s at 25° C., according to claim 1 ,

iv) polymerizing.

17 . The process according to claim 16 made by open molding, pultrusion, hand lay-up and filament winding.

18 . The process according to claim 16 , wherein the polymerizing step takes place at temperature between 40° C. and 140° C.

19 . The process according to claim 16 , wherein the process further comprises a step of post forming.

20 . The process according to claim 16 , wherein the process further comprises a step of welding or gluing or laminating.

21 . A polymeric composite material comprising a thermoplastic (meth)acrylic matrix and a fibrous substrate used as reinforcement, in which the fibrous substrate consists of long fibres having an aspect ratio of at least 1000, said composite material being wherein the thermoplastic (meth)acrylic matrix is obtained after polymerization of the liquid composition LC1, said fibrous substrate preimpregnated with the liquid composition LC as claimed in claim 1 .

22 . A mechanical part or structural element made of composite material as claimed in claim 21 .

23 . The part as claimed in claim 22 , said part being a motor vehicle part, boat part, train part, sport article, plane or helicopter part, space ship or rocket part, photovoltaic module part, a material for construction or building, dowels and stirrups for civil engineering and high rise construction, wind turbine part for example spar cap of girder of wind turbine blade, furniture part, construction or building part, telephone or cellphone part, computer or television part, printer or photocopier part.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2021
From: GERARD, PIERRE
To: ARKEMA FRANCE
Reel/Frame 057446/0286 →
Priority Claims (1)
FR 1902460 · Mar 11, 2019 · national
Continuity (1)
Related Publication 20220162365A1 · May 26, 2022
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