Polymerizable inorganic-particle dispersant, inorganic-organic composite particles containing said polymerizable inorganic-particle dispersant, and inorganic-organic resin composite material
The present invention provides a polymerizable inorganic particle dispersant that can achieve an inorganic-organic composite particle and inorganic-organic resin composite material, which have a high refractive index and a high Abbe's number, i.e., which can achieve both of a high refractive index and a high Abbe's number that is non-conventional in a composite with an inorganic particle. The present invention relates to a polymerizable inorganic particle dispersant comprising a compound which includes the following functional groups A, B and Q: A: Polymerizable functional group; B: Carboxyl group, Oxo acid group containing a phosphorous or Oxo acid group containing sulfur; and C: Sulfur-containing divalent or more aliphatic hydrocarbon group, which may contain a hetero atom other than sulfur.
1. A polymerizable inorganic-particle dispersant, comprising a compound which includes the following functional groups A, B, and Q:
A: a polymerizable functional group;
B: a carboxyl group, an oxo acid group containing phosphorus, or an oxo acid group containing sulfur; and
Q: a sulfur-containing divalent or more cycloaliphatic hydrocarbon group optionally containing a hetero atom other than sulfur,
wherein a proportion of sulfur atoms contained in the polymerizable inorganic-particle dispersant is 20% by mass or higher and 70% by mass or less, in terms of sulfur atom content.
2. The polymerizable inorganic-particle dispersant according to claim 1 , wherein:
the compound including the functional groups A, B, and Q is a compound represented by the following formula (I) or (II):
(A 1 ) n1 -Q 1 -(B 1 ) m1 (I),
A 1 represents a polymerizable functional group,
B 1 represents a carboxyl group, an oxo acid group containing phosphorus, or an oxo acid group containing sulfur,
Q 1 represents a sulfur-containing cycloaliphatic hydrocarbon group which has a valence of (n1+m1) and may contain a hetero atom other than sulfur,
n1 and m1 each independently represent an integer of 1-10, and
with the proviso that when n1 and m1 are integers of 2 or larger, the multiple A 1 or B 1 moieties present in the molecule may be the same or different; and
{(A 2 ) n2 -Q 2 } m2 -B 2 (II),
A 2 represents a polymerizable functional group,
B 2 represents a phosphorus-containing oxo acid group having a valence of m2,
Q 2 represents a sulfur-containing cycloaliphatic hydrocarbon group which has a valence of (n2+1) and may contain a hetero atom other than sulfur;
n2 represents an integer of 1-10,
m2 represents an integer of 2-10, and
with the proviso that the multiple A 2 or Q 2 moieties present in the molecule may be the same or different.
3. The polymerizable inorganic-particle dispersant according to claim 2 , wherein Q 1 in formula (I) or Q 2 in formula (II) respectively is a group represented by the following formula (III) or a group represented by the following formula (IV):
ring G represents a saturated, 3- to 8-membered monocycle or bridged ring, or represents a fused ring or spiro ring comprising two or three monocycles or bridged rings bonded together, wherein part of methylene groups constituting the ring has been replaced with a divalent group comprising a sulfur atom, and part of the methylene groups constituting the ring may further include a divalent group comprising an oxygen atom, a nitrogen atom, or a phosphorus atom,
L represents a direct bond, a sulfide group, an ether group, or an aliphatic hydrocarbon group which may have a hetero atom, and the multiple L moieties contained in the molecule may be the same or different, and
t is (n1+m1) when the formula (III) is Q1, or is (n2+1) when the formula (III) is Q2;
—[S] p —[CR 2 ] q -[E] r - (IV),
R represents a hydrogen atom or a hydrocarbon group which optionally comprise a hetero atom,
E represents a sulfur atom or an oxygen atom,
p represents an integer of 1-3,
q represents an integer of 1-3,
r represents 0 or 1,
multiple R moieties contained in the molecule may be the same or different, and
S, CR 2 , and E in formula (IV) are bonded in any sequence.
4. The polymerizable inorganic-particle dispersant according to claim 3 , wherein the functional group Q comprises the hetero atom other than sulfur atom which is any of an oxygen atom, a phosphorus atom, and a nitrogen atom.
5. The polymerizable inorganic-particle dispersant according to claim 1 , wherein the sulfur-containing cycloaliphatic hydrocarbon group comprises at least one of a dithiane ring, a dithiolane ring, a trithiolane ring, a thiaspiro ring, a dithiaspiro ring, a trithiaspiro ring, a tetrathiaspiro ring, a dithietane ring, a thiirane ring, and a thiolane ring.
6. The polymerizable inorganic-particle dispersant according to claim 2 , wherein the sulfur-containing cycloaliphatic hydrocarbon group comprises at least one of a dithiane ring, a dithiolane ring, a trithiolane ring, a thiaspiro ring, a dithiaspiro ring, a trithiaspiro ring, a tetrathiaspiro ring, a dithietane ring, a thiirane ring, and a thiolane ring.
7. The polymerizable inorganic-particle dispersant according to claim 5 , wherein the sulfur-containing cycloaliphatic hydrocarbon group contains a sulfur-containing chain aliphatic hydrocarbon group as a substituent.
8. The polymerizable inorganic-particle dispersant according to claim 1 , wherein the polymerizable functional group A is any of a (meth)acrylic group, an oxirane group, a thiirane group, and an isocyanate group.
9. The polymerizable inorganic-particle dispersant according to claim 1 , which has a refractive index of 1.62 or higher.
10. The polymerizable inorganic-particle dispersant according to claim 1 , which has an Abbe's number of 40 or higher.
11. Inorganic-organic composite particles, comprising the polymerizable inorganic-particle dispersant according to claim 1 and inorganic particles.
12. The inorganic-organic composite particles according to claim 11 , wherein the inorganic particles are inorganic particles having a refractive index of 2.0 or higher.
13. The inorganic-organic composite particles according to claim 11 , wherein the inorganic particles are inorganic particles having a diameter of 1-10 nm.
14. The inorganic-organic composite particles according to claim 11 , wherein a content of the inorganic particles is 20-90% by mass based on the polymerizable inorganic-particle dispersant.
15. A dispersion, comprising the inorganic-organic composite particles according to claim 11 and a dispersion medium.
16. The dispersion according to claim 15 , which further comprises a polymerizable monomer.
17. An inorganic-organic resin composite material obtained by curing the inorganic-organic composite particles according to claim 11 .
18. An optical material, comprising the inorganic-organic resin composite material according to claim 17 .
19. The optical material according to claim 18 , which is an optical circuit.
20. The optical material according to claim 18 , which is an optical waveguide.
21. The optical material according to claim 18 , which is a lens.
22. A compound, comprising functional groups A, B, and Q:
A: a polymerizable functional group;
B: a carboxyl group, an oxo acid group containing phosphorus, or an oxo acid group containing sulfur; and
Q: a sulfur-containing divalent or more cycloaliphatic hydrocarbon group optionally containing a hetero atom other than sulfur,
wherein a proportion of sulfur atoms contained in the polymerizable inorganic-particle dispersant is 20% by mass or higher and 70% by mass or less, in terms of sulfur atom content.
23. Inorganic-organic composite particles, comprising a polymerizable inorganic-particle dispersant comprising a compound which includes the following functional groups A, B, and Q:
A: a polymerizable functional group;
B: a carboxyl group, an oxo acid group containing phosphorus, or an oxo acid group containing sulfur; and
Q: a sulfur-containing divalent or more cycloaliphatic hydrocarbon group optionally containing a hetero atom other than sulfur.