# US 5,976,242 A · Setting-retarder and its application to concrete, mortars and/or grouts

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- Number: US 5,976,242 A
- Document ID: US5976242A
- Status: Granted
- Kind: A
- Application number: 08/868,724
- Filed: 1997-06-04
- Granted: 1999-11-02
- Earliest claimed: 1994-07-20
- Assignees: Axim
- Inventors: Alain Blanc; Catherine Fontaine
- Web page: https://patentgrep.com/patent/US5976242A

## CPC

- C04B 24/32: Polyethers, e.g. alkylphenol polyglycolether
- C04B 24/001: {Waste organic materials}
- C04B 24/128: {Heterocyclic nitrogen compounds}
- C04B: LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE {(roofing granules E04D7/005)}; CERAMICS (devitrified glass-ceramics C03C10/00); REFRACTORIES; TREATMENT OF NATURAL STONE

## Abstract

A hydraulic-cement setting retarder included in concrete, mortars, or grouts to control setting time as a function of the retarder dosage. Specifically, the retarder is a cyclic amino resin of formula (I): ##STR1## where (a) R1 is a hydrogen atom, a hydroxymethal radial or a group of formula (II) CH.sub.2 --O--R (II) (b) R.sub.2 is a group of formula (II), (c) R is a linear or branched C1-C4 alkyl radical, or a group of formula (III) ##STR2## (d) R.sub.3 and R.sub.4 each are a hydrogen atom, and C1-C4 linear or branched alkyl radical or a group of formula (III).

## Claims

### Claim 1

A cement composition comprising a settable hydraulic cement in combination with an effective amount to retard setting of the cement of at least one cyclic-amino resin of formula (I) ##STR5## wherein (a) R.sub.1 is a hydrogen atom, a hydroxymethyl radical, a 11-hydroxy-3,6,9-trioxa-undecanoyl oxymethyl radical or a group of the formula (II)
CH.sub.2 --O--R (II)
(b) R.sub.2 is a 11-hydroxyl-3,6,9-trioxa-undecanoyl oxymethyl radical or a group of formula (II), wherein
(c) R is a linear or branched C.sub.1 -C.sub.4 alkyl radical, or a group of formula (III) ##STR6## (d) where R.sub.3 and R.sub.4 each are a hydrogen atom, a C.sub.1 -C.sub.4 linear or branched alkyl radical or a group of formula (III), and R', R" and R'" each represent a hydrogen atom, a C.sub.1 -C.sub.4 linear or branched alkyl radical, n is 0 or 1 and m is 1, 2, 3, or 4.

### Claim 2 (depends on 1)

A cement composition according to claim 1, wherein R.sub.3 and R.sub.4 are identical.

### Claim 3 (depends on 1)

A cement composition according to claim 1, wherein R', R", R'" are identical.

### Claim 4 (depends on 1)

A cement composition according to claim 1, wherein the C.sub.1 -C.sub.4 linear or branched alkyl radical denotes a methyl-, ethyl-, n-propyl-, isopropyl, n-butyl or isobutyl-radical.

### Claim 5 (depends on 1)

A cement composition according to claim 1, wherein R is methyl-, ethyl-, n-propyl-, n-butyl-, isopropyl-, isobutyl-, 2-hydroxyethyl, 2-hydroxypropyl, 2-(2-hydroxyethoxy)ethyl, or 11-hydroxy-3,6,9-trioxa-undecanoyl-radical including their different stereoisomeric forms.

### Claim 6 (depends on 1)

A cement composition according to claim 1, wherein the cyclic amino resins of formula (I) are selected from the groups:
a) bis1,3-methoxymethyl-4,5-dihydroxy-2-imidazolidinone;
b) 1-hydroxymethyl-3(2-hydroxyethoxymethyl)-4,5-dihydroxy-2-imidazolidinone;
c) bis1,3-(2-hydroxyethoxymethyl)-4,5-dihydroxy-2-imidazolidinone;
d) 1-hydroxymethyl-3-2-(2-hydroxyethoxy)ethoxymethyl-4,5-dihydroxy-2-imidazol idinone;
e) bis1,3-2-(2-hydroxyethoxy)ethoxymethyl)-4,5-dihydroxy-2-imidazolidinone;
f) 1-hydroxymethyl-3(11-hydroxy-3,6,9-trioxa-undecanoyl oxymethyl)-4,5-dihydroxy-2-imidazolidinone; and
g) bis1,3-(11-hydroxy-3,6,9-trioxa-undecanoyloxymethyl)-4,5-dihydroxy-2-imida zolidinone.

### Claim 7 (depends on 6)

A cement composition according to claim 6, wherein the cyclic amino resins of formula I are trans isomers.

### Claim 8 (depends on 6)

A cement composition according to claim 6, wherein the cyclic amino resins of formula I are cis isomers.

### Claim 9 (depends on 1)

A cement composition according to claim 1, wherein the cyclic amino resins of formula (I) are defined by the molar ratios of glyoxal (G), formaldehyde (F) and ROH alcohol (A) or urea (U) such at if G/U=1, then 1.5>F/U>2 and 0.5<0.5<A/U<2.

### Claim 10 (depends on 1)

A cement composition according to claim 1, wherein the cyclic amino resins of formula (II) are either mixed with or complexed by a boron derivative selected from the group consisting of boric acid and sodium tetraborate.

### Claim 11 (depends on 10)

The cement composition of claim 10, wherein the cyclic amino resins of formula (II) are either mixed with or complexed by a member selected from the group consisting of boric acid, an alkali metal salt thereof, and an alkaline earth metal salt thereof, wherein 0.025 to 0.25 moles of said member per mole of urea is present in the resin.

### Claim 12 (depends on 1)

The cement composition of claim 1, wherein the amino resins of formula (I) are used to retard the setting of the hydraulic-cement in amounts of about 0.001 to 5%.

### Claim 13 (depends on 1)

The cement composition of claim 1, wherein the cement is a concrete mortar or grout.

### Claim 14 (depends on 13)

A method according to claim 13, wherein said effective amount comprises about 0.001 to about 5% by weight, based on the cement.

### Claim 15

A method for retarding the setting of a hydraulic cement which comprises adding to said cement an effective amount of a setting retarder comprising a cyclic-amino resin of formula I: ##STR7## wherein (a) R.sub.1 is a hydrogen atom, a hydroxymethyl radical, a 11-hydroxy-3,6,9-trioxa-undecanoyl oxymethyl radical or a group of the formula (II)
--CH.sub.2 --O--R (II)
(b) R.sub.2 is a 11-hydroxyl-3,6,9-trioxa-undecanoyl oxymethyl radical or a group of formula (II), wherein
(c) R is a linear or branched C.sub.1 -C.sub.4 alkyl radical, or a group of formula (III) ##STR8## (d) where R.sub.3 and R.sub.4 each are a hydrogen atom, a C.sub.1 -C.sub.4 linear or branched alkyl radical or a group of formula (III), and R', R" and R'" each represent a hydrogen atom, a C.sub.1 -C.sub.4 linear or branched alkyl radical, n is 0 or 1 and m is 1, 2, 3, or 4.