IP Library Granted Patent US 9,138,703
Granted Patent B2
US 9,138,703 · App. 14/211,347 · Granted Sep 22, 2015

Composition made of polyalkoxylated derivatives of trimethylolpropane and fatty alcohols, method for preparing said composition, and use thereof as a reverser in self-reversible reverse latexes

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Quick Facts
Patent No.
US 9,138,703
App. No.
14/211,347
Granted
Sep 22, 2015
Kind
B2
Abstract

A novel composition made of polyalkoxylated derivatives of trimethylolpropane and fatty alcohols, the preparation thereof and the use thereof as a reversing agent for a reversible reverse latex.

Claims (192)

1. A self invertible inverse latex comprising as an inverting agent a surfactant composition (C), alone or as a mixture with other emulsifying agents capable of preparing an oil-in-water (O/W) emulsifying system), said surfactant composition (C) comprising, per 100 mol %:

1) a proportion of greater than or equal to 10 mol % and of less than or equal to 50 mol % of a composition (C II ) comprising, per 100 mol %:

α) from 60 mol % to 100 mol % of a compound of formula (II):

in which:

R2 represents a linear or branched alkyl radical comprising 12 carbon atoms,

T 1 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m1 —H radical in which m1 is an integer of greater than or equal to zero and less than or equal to ten,

T 2 , which is identical to or different from T 1 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m2 —H radical in which m2 is an integer of greater than or equal to zero and less than or equal to ten, and

T 3 , which is identical to or different from T 1 and T 2 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m3 —H radical in which m3 is an integer of greater than or equal to zero and less than or equal to ten,

wherein m1 +m2 +m3 is greater than 0 and less than or equal to ten;

β) optionally up to 40 mol % of a compound of formula (II′):

in which:

R′ 2 represents a linear or branched alkyl radical comprising 14 carbon atoms,

T′ 1 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m1 —H radical in which m1 is an integer of greater than or equal to zero and less than or equal to ten,

T′ 2 , which is identical to or different from T′ 1 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m2 —H radical in which m2 is an integer of greater than or equal to zero and less than or equal to ten, and

T′ 3 , which is identical to or different from T′ 1 and T′ 2 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m3 —H radical in which m3 is an integer of greater than or equal to zero and less than or equal to ten,

wherein the sum m1 +m2 +m3 is greater than 0 and less than or equal to ten; and

γ) optionally up to 10 mol % of a compound of formula (II″):

in which:

R″ 2 represents a linear or branched alkyl radical comprising 16 carbon atoms,

T″ 1 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m1 —H radical in which m1 is an integer of greater than or equal to zero and less than or equal to ten,

T″ 2 , which is identical to or different from T″ 1 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m2 —H radical in which m2 is an integer of greater than or equal to zero and less than or equal to ten, and

T″ 3 , which is identical to or different from T″ 1 and T″ 2 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m3 —H radical in which m3 is an integer of greater than or equal to zero and less than or equal to ten,

Wherein the sum m1 +m2 +m3 is greater than 0 and less than or equal to ten;

2) a proportion of greater than or equal to 50 mol % and of less than or equal to 90 mol % of a composition (C III ) comprising, per 100 mol %:

α) from 60 mol % to 100 mol % of a compound of formula (III):

or of its isomer of formula (IV):

or of the mixture of these two isomers, in which formulae (III) and (IV):

R2 represents a linear or branched alkyl radical comprising 12 carbon atoms, T 4 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m4 —H radical in which m4 is an integer of greater than or equal to zero and less than or equal to ten,

T 5 , which is identical to or different from T 4 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m5 —H radical in which m5 is an integer of greater than or equal to zero and less than or equal to ten,

T 6 , which is identical to or different from T 4 and T 5 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m6 —H radical in which m6 is an integer of greater than or equal to zero and less than or equal to ten,

T 7 , which is identical to or different from T 4 , T 5 and T 6 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m7 —H radical in which m7 is an integer of greater than or equal to zero and less than or equal to ten,

wherein the sum m4 +m5 +m6 +m7 is greater than 0 and less than or equal to ten;

β) optionally up to 40 mol % of a compound of formula (III′):

or of its isomer of formula (IV′):

or of the mixture of these two isomers,

in which formulae (III′) and (IV′):

R′ 2 represents a linear or branched alkyl radical comprising 14 carbon atoms,

T′ 4 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m4 —H radical in which m4 is an integer of greater than or equal to zero and less than or equal to ten,

T′ 5 , which is identical to or different from T′ 4 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m5 —H radical in which m5 is an integer of greater than or equal to zero and less than or equal to ten,

T′ 6 , which is identical to or different from T′ 4 and T′ 5 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m6 —H radical in which m6 is an integer of greater than or equal to zero and less than or equal to ten, and

T′ 7 , which is identical to or different from T′ 4 , T′ 5 and T′ 6 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m7 —H radical in which m7 is an integer of greater than or equal to zero and less than or equal to ten,

wherein the sum m4 +m5 +m6 +m7 is greater than 0 and less than or equal to ten; and

γ) optionally up to 10 mol % of a compound of formula (III″):

or of its isomer of formula (IV″):

or of the mixture of these two isomers,

in which formulae (III″) and (IV″):

R″ 2 represents a linear or branched alkyl radical comprising 16 carbon atoms,

T″4 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m4 —H radical in which m4 is an integer of greater than or equal to zero and less than or equal to ten,

T″ 5 , which is identical to or different from T″ 4 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m5 —H radical in which m5 is an integer of greater than or equal to zero and less than or equal to ten,

T″ 6 , which is identical to or different from T″ 4 and T″ 5 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m6 —H radical in which m6 is an integer of greater than or equal to zero and less than or equal to ten, and

T″ 7 , which is identical to or different from T″ 4 , T″ 5 and T′ 6 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m7 —H radical in which m7 is an integer of greater than or equal to zero and less than or equal to ten,

wherein the sum m4 +m5 +m6 +m7 is greater than 0 and less than or equal to ten.

2. The self invertible inverse latex according to claim 1 , wherein the surfactant composition (C) additionally comprises:

3) up to 5 mol % of a composition (C v ) comprising, per 100 mol %:

α) from 60 mol % to 100 mol % of a compound of formula (V):

in which:

R2 represents a linear or branched alkyl radical comprising 12 carbon atoms,

T 8 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m8 —H radical in which m8 is an integer of greater than or equal to zero and less than or equal to ten,

T 9 , which is identical to or different from T 8 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m9 —H radical in which m9 is an integer of greater than or equal to zero and less than or equal to ten, and

wherein the sum m8 +m9 is greater than 0 and less than or equal to ten;

β) -optionally up to 40 mol % of a compound of formula (V′):

in which:

R′ 2 represents a linear or branched alkyl radical comprising 14 carbon atoms,

T′ 8 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m8 —H radical in which m8 is an integer of greater than or equal to zero and less than or equal to ten,

T′ 9 , which is identical to or different from T′ 8 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m9 —H radical in which m9 is an integer of greater than or equal to zero and less than or equal to ten, and

Wherein the sum m8 +m9 is greater than 0 and less than or equal to ten; and

γ) optionally up to 10 mol % of a compound of formula (V″):

in which:

R″ 2 represents a linear or branched alkyl radical comprising 16 carbon atoms,

T″ 8 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m8 —H radical in which m8 is an integer of greater than or equal to zero and less than or equal to ten,

T″ 9 , which is identical to or different from T″ 8 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m9 —H radical in which m9 is an integer of greater than or equal to zero and less than or equal to ten, and

wherein the sum m8 +m9 is greater than 0 and less than or equal to ten.

3. The self invertible inverse latex according to claim 1 , wherein the surfactant composition (C) additionally comprises:

4) up to 5 mol % of a composition (C VI ) comprising, per 100 mol %:

α) from 60 mol % to 100 mol % of a compound of formula (VI):

R2-(—CH 2 —CH 2 —O—) m10 —H   (VI),

in which R2 represents a linear or branched alkyl radical comprising 12 carbon atoms and m10 is an integer of greater than or equal to zero and less than or equal to ten;

α) optionally up to 40 mol % of a compound of formula (VI′):

R 2 1 —(—CH 2 —CH 2 —O—) m10 —H   (VI′),

in which R′ 2 represents a linear or branched alkyl radical comprising 14 carbon atoms and m10 is an integer of greater than or equal to zero and less than or equal to ten; and

γ) optionally up to 10 mol % of a compound of formula (VI″):

R″ 2 —(—CH 2 CH 2 —O—) m10 —H   (VI ″),

in which R″ 2 represents a linear or branched alkyl radical comprising 16 carbon atoms and m10 is an integer of greater than or equal to zero and less than or equal to ten.

4. The self invertible inverse latex according to claim 1 , wherein the surfactant composition (C) comprises:

1) a proportion of greater than or equal to 20 mol % and of less than or equal to 50 mol % of the composition (C II ); and

2) a proportion of greater than or equal to 50 mol % and of less than or equal to 80 mol % of the composition (C III ).

5. The self invertible inverse latex according to claim 4 , wherein:

1) said composition (C II ) comprises, per 100 mol %:

α) from 60 mol % to 80 mol % of the compound of formula (II),

β) from 15 mol % to 30 mol % of the compound of formula (II′), and

γ) up to 10 mol % of the compound of formula (II″), and

2) said composition (C III ) comprises, per 100 mol %:

α) from 60 mol % to 80 mol % of the compound of formula (III), of its isomer of formula (IV) or of the mixture of these isomers,

β) from 15 mol % to 30 mol % of the compound of formula (III′), of its isomer of formula (IV′) or of the mixture of these isomers, and

γ) up to 10 mol % of the compound of formula (III″), of its isomer of formula (IV″) or of the mixture of these isomers.

6. A surfactant composition (C), said surfactant composition (C) being an oil-in-water (O/W) emulsifying agent and comprising, per 100 mol %:

1) a proportion of greater than or equal to 10 mol % and of less than or equal to 50 mol % of a composition (C II ) comprising, per 100 mol %:

α) from 60 mol % to 100 mol % of a compound of formula (II):

in which:

R2 represents a linear or branched alkyl radical comprising 12 carbon atoms,

T 1 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m1 —H radical in which m1 is an integer of greater than or equal to zero and less than or equal to ten,

T 2 which is identical to or different from T 1 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m2 —H radical in which m2 is an integer of greater than or equal to zero and less than or equal to ten, and

T 3 , which is identical to or different from T 1 and T 2 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m3 —H radical in which m3 is an integer of greater than or equal to zero and less than or equal to ten,

wherein m1 +m2 +m3 is greater than 0 and less than or equal to ten;

β) optionally up to 40 mol % of a compound of formula (II′):

in which:

R′ 2 represents a linear or branched alkyl radical comprising 14 carbon atoms,

T′ 1 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m1 —H radical in which m1 is an integer of greater than or equal to zero and less than or equal to ten,

T′ 2 , which is identical to or different from T′ 1 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m2 —H radical in which m2 is an integer of greater than or equal to zero and less than or equal to ten, and

T′ 3 , which is identical to or different from T′ 1 and T′ 2 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m3 —H radical in which m3 is an integer of greater than or equal to zero and less than or equal to ten,

wherein the sum m1 +m2 +m3 is greater than 0 and less than or equal to ten; and

γ) optionally up to 10 mol % of a compound of formula (II″):

in which:

R″ 2 represents a linear or branched alkyl radical comprising 16 carbon atoms,

T″ 1 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m1 —H radical in which m1 is an integer of greater than or equal to zero and less than or equal to ten,

T″ 2 , which is identical to or different from T″ 1 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m2 —H radical in which m2 is an integer of greater than or equal to zero and less than or equal to ten, and

T″ 3 , which is identical to or different from T″ 1 and T″ 2 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m3 —H radical in which m3 is an integer of greater than or equal to zero and less than or equal to ten,

Wherein the sum m1 +m2 +m3 is greater than 0 and less than or equal to ten;

2) a proportion of greater than or equal to 50 mol % and of less than or equal to 90 mol % of a composition (C III ) comprising, per 100 mol %:

α) from 60 mol % to 100 mol % of a compound of formula (III):

or of its isomer of formula (IV):

or of the mixture of these two isomers, in which formulae (III) and (IV):

R2 represents a linear or branched alkyl radical comprising 12 carbon atoms,

T 4 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m4 —H radical in which m4 is an integer of greater than or equal to zero and less than or equal to ten,

T 5 , which is identical to or different from T 4 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m5 —H radical in which m5 is an integer of greater than or equal to zero and less than or equal to ten,

T 6 , which is identical to or different from T 4 and T 5 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m6 —H radical in which m6 is an integer of greater than or equal to zero and less than or equal to ten,

T 7 , which is identical to or different from T 4 , T 5 and T 6 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m7 —H radical in which m7 is an integer of greater than or equal to zero and less than or equal to ten,

wherein the sum m4 +m5 +m6 +m7 is greater than 0 and less than or equal to ten;

β) optionally up to 40 mol % of a compound of formula (III′):

or of its isomer of formula (IV′):

or of the mixture of these two isomers,

in which formulae (III′) and (IV′):

R′ 2 represents a linear or branched alkyl radical comprising 14 carbon atoms,

T′ 4 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m4 —H radical in which m4 is an integer of greater than or equal to zero and less than or equal to ten,

T′ 5 , which is identical to or different from T′ 4 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m5 —H radical in which m5 is an integer of greater than or equal to zero and less than or equal to ten,

T′ 6 , which is identical to or different from T′ 4 and T′ 5 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m6 —H radical in which m6 is an integer of greater than or equal to zero and less than or equal to ten, and

T′ 7 , which is identical to or different from T′ 4 , T′ 5 and T′ 6 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m7 —H radical in which m7 is an integer of greater than or equal to zero and less than or equal to ten,

wherein the sum m4 +m5 +m6 +m7 is greater than 0 and less than or equal to ten; and

γ) optionally up to 10 mol % of a compound of formula (III″):

or of its isomer of formula (IV″):

or of the mixture of these two isomers,

in which formulae (III″) and (IV″):

R″ 2 represents a linear or branched alkyl radical comprising 16 carbon atoms,

T″4 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m4 —H radical in which m4 is an integer of greater than or equal to zero and less than or equal to ten,

T″ 5 , which is identical to or different from T′ 4 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m5 —H radical in which m5 is an integer of greater than or equal to zero and less than or equal to ten,

T″ 6 , which is identical to or different from T″ 4 and T″ 5 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m6 —H radical in which m6 is an integer of greater than or equal to zero and less than or equal to ten, and

T″ 7 , which is identical to or different from T″ 4 , T″ 5 and T′ 6 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m7 —H radical in which m7 is an integer of greater than or equal to zero and less than or equal to ten,

wherein the sum m4 +m5 +m6 +m7 is greater than 0 and less than or equal to ten.

7. The surfactant composition (C) according to claim 6 , further comprising:

3) up to 5 mol % of a composition (C v ) comprising, per 100 mol %:

α) from 60 mol % to 100 mol % of a compound of formula (V):

in which:

R2 represents a linear or branched alkyl radical comprising 12 carbon atoms,

T 8 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m8 —H radical in which m8 is an integer of greater than or equal to zero and less than or equal to ten,

T 9 , which is identical to or different from T 8 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m9 —H radical in which m9 is an integer of greater than or equal to zero and less than or equal to ten, and

wherein the sum m8 +m9 is greater than 0 and less than or equal to ten;

β) -optionally up to 40 mol % of a compound of formula (V′):

in which:

R′ 2 represents a linear or branched alkyl radical comprising 14 carbon atoms,

T′ 8 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m8 —H radical in which m8 is an integer of greater than or equal to zero and less than or equal to ten,

T′ 9 , which is identical to or different from T′ 8 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m9 —H radical in which m9 is an integer of greater than or equal to zero and less than or equal to ten, and

Wherein the sum m8 +m9 is greater than 0 and less than or equal to ten; and

γ) optionally up to 10 mol % of a compound of formula

(V″):

in which:

R″ 2 represents a linear or branched alkyl radical comprising 16 carbon atoms,

T″ 8 represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m8 —H radical in which m8 is an integer of greater than or equal to zero and less than or equal to ten,

T″ 9 , which is identical to or different from T″ 8 , represents a hydrogen atom or a (—CH 2 —CH 2 —O—) m9 —H radical in which m9 is an integer of greater than or equal to zero and less than or equal to ten, and

wherein the sum m8 +m9 is greater than 0 and less than or equal to ten.

8. The surfactant composition (C) according to claim 6 , further comprising:

4) up to 5 mol % of a composition (C VI ) comprising, per 100 mol %:

α) from 60 mol % to 100 mol % of a compound of formula (VI):

R2-(—CH 2 —CH 2 —O—) m10 —H   (VI),

in which R2 represents a linear or branched alkyl radical comprising 12 carbon atoms and m10 is an integer of greater than or equal to zero and less than or equal to ten;

β) optionally up to 40 mol % of a compound of formula (VI′):

R′ 2 —(—CH 2 —CH 2 —O—) m10 —H   (VI),

in which R′ 2 represents a linear or branched alkyl radical comprising 14 carbon atoms and m10 is an integer of greater than or equal to zero and less than or equal to ten; and

γ) optionally up to 10 mol % of a compound of formula (VI″):

R″ 2 —(—CH 2 —CH 2 —O—) m10 —H   (VI″),

in which R″ 2 represents a linear or branched alkyl radical comprising 16 carbon atoms and m10 is an integer of greater than or equal to zero and less than or equal to ten.

9. The surfactant composition (C) according to claim 6 , comprising:

1) a proportion of greater than or equal to 20 mol % and of less than or equal to 50 mol % of the composition (C II ); and

2) a proportion of greater than or equal to 50 mol % and of less than or equal to 80 mol % of a composition (C III ).

10. The surfactant composition (C) according to claim 9 , wherein:

1) said composition (C II ) comprises, per 100 mol %:

α) from 60 mol % to 80 mol % of the compound of formula (II),

β) from 15 mol % to 30 mol % of the compound of formula (II′), and

γ) up to 10 mol % of the compound of formula (II″), and

2) said composition (C III ) comprises, per 100 mol %:

α) from 60 mol % to 80 mol % of the compound of formula (III′), of its isomer of formula (IV) or of the mixture of these isomers,

γ) from 15 mol % to 30 mol % of the compound of formula (III″), of its isomer of formula (IV″) or of the mixture of these isomers, and

γ) up to 10 mol % of the compound of formula (III″), of its isomer of formula (IV″) or of the mixture of these isomers.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE SECOND INVENTOR NAME FROM HERVE MALLO TO HERVE ROLLAND PREVIOUSLY RECORDED ON REEL 034070 FRAME 0077. ASSIGNOR(S) HEREBY CONFIRMS THE NAME IS CORRECT ON THE EXECUTED ASSIGNMENT. Recorded Jan 15, 2015
From: MALLO, PAUL; ROLLAND, HERVE; DA COSTA, GEORGES; BRAUN, OLIVIER
To: SOCIETE D'EXPLOITATION DE PRODUITS POUR LES INDUSTRIES CHIMIQUES SEPPIC
Reel/Frame 034767/0337 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2014
From: MALLO, PAUL; MALLO, HERVE; DA COSTA, GEORGES; BRAUN, OLIVIER
To: SOCIETE D'EXPLOITATION DE PRODUITS POUR LES INDUSTRIES CHIMIQUES SEPPIC
Reel/Frame 034070/0077 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2014
From: MALLO, PAUL; ROLLAND, HERVE; DE COSTA, GEORGES; BRAUN, OLIVIER
To: SOCIETE D'EXPLOITATION DE PRODUITS POUR LES INDUSTRIES CHIMIQUES SEPPIC
Reel/Frame 032440/0328 →