Eraser tool containing polyetheramine

Patent metadata

Field	Value
Publication number	US-11787226-B2
Application number	US-201917255527-A
Country	US
Kind code	B2
Filing date	Jul 30, 2019
Priority date	Jul 31, 2018
Publication date	Oct 17, 2023
Grant date	Oct 17, 2023

Abstract

There is an erasing tool having a polyetheramine for erasing a thermochromic ink composition capable of undergoing a color change that cannot be reversed by application of a temperature change. There also is a writing instrument having a thermochromic ink composition and an erasing tool. Finally, there is a method for irreversibly erasing a written line made with a thermochromic ink composition and erased with an erasing tool.

First claim

The invention claimed is:

1. An erasing composition comprising:
(a) from 10 to 80% by weight of at least one rubber, (b) from 20 to 80% by weight of at least one filler, and (c) from 1 to 50% by weight of at least one polyetheramine comprising a polyether backbone based on propylene oxide, ethylene oxide, or mixed propylene oxide/ethylene oxide units, and at least one primary or secondary amino group attached to the end of the polyether backbone.

2. An erasing composition as claimed in claim 1 , wherein the polyetheramine has one of the following formulas (I), (II) or (III):

with:
n varying from 5 to 40, and
R representing H or a linear or branched alkyl chain comprising 1 to 4 carbon atoms,

with:
m=0 or 1,
x, y and z varying from 1 to 80, and (x+y+z) varying from 3 to 90,
R′ representing H or an alkyl chain comprising 1 or 2 carbon atoms, and
R″ representing H or a linear or branched alkyl chain comprising 1 to 4 carbon atoms,

with p and q varying from 1 to 6.

3. An erasing composition as claimed in claim 1 or claim 2 comprising:
(a) from 10 to 80% by weight of at least one rubber, (b) from 20 to 80% by weight of at least one filler, and (c) from 1 to 50% by weight of at least one polyetheramine of formula:

with:
n varying from 20 to 40, and
R representing H or a linear or branched alkyl chain comprising 1 to 4 carbon atoms.

4. The erasing composition as claimed in claim 1 , wherein the rubber (a) is selected from ethylene-propylene-diene monomer (EPDM) rubber, Vulcanized Thermoplastic Elastomer (TPV) which is a blend of ethylene-propylene-diene monomer (EPDM) rubber and polypropylene (PP), ethylene-propylene rubber (EPR), poly(styrene-butadiene-styrene) (SBS), styrene ethylene butylene styrene (SEBS), natural rubber (NR), polyisoprene (IR), polyvinyl chloride, styrene-based thermoplastic elastomers including styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene-propylene-styrene (SEPS), styrene-ethylene-ethylene-propylene-styrene (SEEPS), and mixtures thereof.

5. The erasing composition as claimed in claim 1 , wherein the filler is selected from the group consisting of calcium carbonate, calcium silicate, sodium sulphate, clay, talc, kaolin, silica, mica, calcite, wollastonite, and bentonite.

6. The erasing composition as claimed in claim 1 , wherein the polyetheramine (c) is of formula:

with:
n varying from 25 to 35, and
R is CH 3 .

7. The erasing composition as claimed in claim 1 , further comprising from 0.1 to 20% by weight of at least one pigment (d).

8. An erasing tool comprising as a solid core an erasing composition as claimed claim 1 .

9. A method for preparing an erasing tool comprising the steps of:
(i) preparing an erasing composition as claimed in claim 1 by mixing, at a temperature ranging from 100 to 250° C.:
(a) from 10 to 80% by weight of at least one rubber,
(b) from 20 to 80% by weight of at least one filler,
(c) from 1 to 50% by weight of at least one polyetheramine comprising a polyether backbone based on propylene oxide, ethylene oxide, or mixed propylene oxide/ethylene oxide units, and at least one primary or secondary amino group attached to the end of the polyether backbone, and

(ii) shaping the erasing composition obtained at the end of step (i), obtaining an erasing tool.

10. A method for preparing an erasing tool as claimed in claim 9 , wherein the at least one polyetheramine has one of the following formulas (I), (II) and (III):

with:
n varying from 5 to 40, and
R representing H or a linear or branched alkyl chain comprising 1 to 4 carbon atoms,

with:
m=0 or 1,
x, y and z varying from 1 to 80, and (x+y+z) varying from 3 to 90,
R′ representing H or an alkyl chain comprising 1 or 2 carbon atoms, and
R″ representing H or a linear or branched alkyl chain comprising 1 to 4 carbon atoms,

with p and q varying from 1 to 6.

11. A method for preparing an erasing tool as claimed in claim 10 , wherein the at least one polyetheramine is of formula (I).

12. Method of irreversibly erasing a thermochromic ink composition on a paper, comprising contacting the thermochromic ink composition with the erasing tool as claimed in claim 8 .

13. A writing instrument comprising:
an ink reservoir containing a thermochromic ink composition comprising color-changing core-shell microcapsules dispersed in a carrier, and
an erasing tool as claimed in claim 8 .

14. A writing instrument as claimed in claim 13 , wherein the core-shell microcapsules comprises:
an electron donative coloring organic compound,
an electron accepting compound, and
a reaction medium controlling the color reaction between the electron donative coloring organic compound and the electron accepting compound.

15. A writing instrument as claimed in claim 14 , wherein the reaction medium is a wax has a melting point ranging from 40 to 70° C.

16. A writing instrument as claimed in claim 14 , wherein the electron donative coloring organic compound is selected from the group consisting of 3-(4-diethylamino-2-ethoxyphenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide (Blue 63, CAS number 69898-40-4), 2′-(dibenzylamino)-6′-(diethylamino)fluorane (CAS number 34372-72-0), N,N-dimethyl-4-[2-[2-(octyloxy)phenyl]-6-phenyl-4-pyridinyl]benzenamine (Yellow CK37, CAS number 144190-25-0), 7-(4-diethylamino-2-hexyloxyphenyl)-7-(1-ethyl-2-methyl-1H-indol-3-yl)-7H-furo[3,4-b]pyridin-5-one (Blue 203, CAS number 98660-18-5), 2-(2,4-dimethylphenylamino)-3-methyl-6-diethylaminofluoran (Black 15, CAS number: 36431-22-8), and 3,3-bis-(1-butyl-2-methyl-indol-3-yl)-3H-isobenzofuran-1-one (Red 40, CAS number 50292-91-6).

17. A writing instrument as claimed in claim 14 , wherein the electron accepting compound is selected from the group consisting of 2,2-bis(4-hydroxy-3-methylphenyl)propane (Bisphenol C, CAS number 79-97-0), 4-hexyl-1,3-dihydroxybenzene (4-hexylresorcinol, CAS number 136-77-6), 4,4′-cyclohexylidenebisphenol (BPZ, CAS number 843-55-0), 4,4′-(hexafluoroisopropylidene)diphenol (Bisphenol AF, CAS number 1478-61-1), 4,4′-(1-phenylethylidene)bisphenol (CAS number 1571-75-1), 2,2′-dihydroxybiphenyl (CAS number 1806-29-7), 4,4′-(1,4-phenylenediisopropylidene)bisphenol (CAS number 2167-51-3), 1,1-bis(4-hydroxy-3-methylphenyl)cyclohexane (CAS number 2362-14-3), 9,9-bis(4-hydroxyphenyl)fluorene (CAS number 3236-71-3), 4,4′-(1,3-phenylenediisopropylidene)bisphenol (CAS number 13595-25-0), 1,1,1-tris(4-hydroxyphenyl)ethane (CAS number 27955-94-8), 4,4′-(2-ethylhexylidene)diphenol (CAS number 74462-02-5), α,α,α′-tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene (CAS number 110726-28-8), 3,5,4′-trihydroxy-trans-stilbene (resveratrol, CAS number 501

Assignees

• SOCIéTé BIC

Inventors

• Caffier Guillaume
• Sauvage Aurore

Classifications

• B43L19/0025 Primary

  Eraser or rubber material, e.g. comprising hard particles · CPC title

• B43K29/02

  with rubbers · CPC title

• C08K3/22

  of metals · CPC title

• C08K3/26

  Carbonates; Bicarbonates · CPC title

• C08K5/18

  with aromatically bound amino groups · CPC title