公开(公告)号：US07371466B2

公开(公告)日：2008-05-13

申请号：US10412331

申请日：2003-04-14

Applicant: Brendan J. Kneafsey ,  Gerry Coughlan ,  Thomas B. Harty

Inventor： Brendan J. Kneafsey ,  Gerry Coughlan ,  Thomas B. Harty

IPC: B32B27/30 ,  C08F4/42

CPC classification number: C09J4/00 ,  Y10T428/31928 ,  Y10T428/31935 ,  C08F220/00

Abstract: Quaternary boron salts are used as initiators of polymerisation in adhesive compositions for bonding low surface energy substrates such as polyolefins. The quaternary boron salts are of the formula I wherein R1 is C1-C10 alkyl, R2, R3 and R4, which may be the same or different, are, C1-C10 alkyl or C3-C10 cycloalkyl, phenyl, or phenyl-substituted C1-C10 alkyl or C3-C10 cycloalkyl, provided that any two of R1-R4 may optionally be part of a carbocyclic ring, and M+ is a metal ion or a quaternary ammonium ion. When M+ is a quaternary ammonium ion, the initiator may be used in a two-part composition having a (meth)acrylate monomer in both parts and the initiator compound in one part, the two parts being in a weight ratio of about 1:1.Particular examples of initiator compounds include sodium tetraethyl borate, lithium tetraethyl borate, lithium phenyl triethyl borate, tetramethylammonium phenyl triethyl borate, and tetra methyl ammonium phenyl tri-n-butyl borate, the last-mentioned of which is a novel compound.

Abstract translation: 在粘合剂组合物中用作键合低表面能基底如聚烯烃的季铵硼盐作为聚合引发剂。 季硼盐具有式I的化合物，其中R 1是C 1 -C 10烷基，R 2， R 3和R 4可以相同或不同，是C 1 -C 10烷基， 烷基或C 3 -C 10环烷基，苯基或苯基取代的C 1 -C 10烷基或 C 3 -C 10环烷基，条件是R 1〜R 4中的任意两个可以任选地为 碳环，M + +是金属离子或季铵离子。 当M + +是季铵离子时，引发剂可以在两部分中具有（甲基）丙烯酸酯单体和引发剂化合物的两部分组合物中一起使用，两部分在 重量比约为1:1。 引发剂化合物的具体实例包括硼酸四乙酯，硼酸四乙酯锂，苯基三乙基硼酸锂，硼酸四甲基铵，硼酸三甲基铵和硼酸四正丁基铵，其中最后提到了新的化合物。

公开(公告)号：US07267886B2

公开(公告)日：2007-09-11

申请号：US11003959

申请日：2004-12-03

Applicant: Brendan J. Kneafsey ,  Gerry Coughlan

Inventor： Brendan J. Kneafsey ,  Gerry Coughlan

IPC: B32B27/08

CPC classification number: C08F4/52 ,  C09J4/00 ,  Y10T428/31504 ,  Y10T428/31855 ,  Y10T428/31928 ,  Y10T428/31935 ,  C08F220/18

Abstract: Quaternary boron salts are used as initiators of polymerisation in adhesive compositions for bonding low surface energy substrates such as polyolefins. The quaternary boron salts are of the formula I wherein R1 is C1–C10 alkyl, R2, R3 and R4, which may be the same or different, are, C1–C10 alkyl or C3–C10 cycloalkyl, phenyl, or phenyl-substituted C1–C10 alkyl or C3–C10 cycloalkyl, provided that any two of R1–R4 may optionally be part of a carbocyclic ring, and M+ is a metal ion or a quaternary ammonium ion. Particular examples of initiator compounds include sodium tetraethyl borate and lithium tetraethyl borate, lithium phenyl triethyl borate and tetraethylammonium phenyl triethyl borate.

Abstract translation: 在粘合剂组合物中用作键合低表面能基底如聚烯烃的季铵硼盐作为聚合引发剂。 季硼盐具有式I的化合物，其中R 1是C 1 -C 10烷基，R 2， R 3和R 4可以相同或不同，是C 1 -C 10烷基， 烷基或C 3 -C 10环烷基，苯基或苯基取代的C 1 -C 10烷基或 C 3 -C 10环烷基，条件是R 1〜R 4中的任意两个可以任选地为 碳环，M + +是金属离子或季铵离子。 引发剂化合物的具体实例包括硼酸四乙酯和硼酸四乙酯锂，苯基硼酸三乙酯和硼酸四乙基铵苯酯。

公开(公告)号：US07189463B2

公开(公告)日：2007-03-13

申请号：US10399230

申请日：2001-10-23

Applicant: Brendan J. Kneafsey ,  Gerry Coughlan

Inventor： Brendan J. Kneafsey ,  Gerry Coughlan

IPC: C08F4/00

CPC classification number: C08F4/52 ,  C09J4/00 ,  Y10T428/31504 ,  Y10T428/31855 ,  Y10T428/31928 ,  Y10T428/31935 ,  C08F220/18

Abstract: Quaternary boron salts are used as initiators of polymerisation in adhesive compositions for bonding low surface energy substrates such as polyolefins. The quaternary boron salts are of the formula I wherein R1 is C1–C10 alkyl, R2, R3 and R4, which may be the same or different, are, C1–C10 alkyl or C3–C10 cycloalkyl, phenyl, or phenyl-substituted C1–C10 alkyl or C3–C10 cycloalkyl, provided that any two of R1–R4 may optionally be part of a carbocyclic ring, and M+ is a metal ion or a quaternary ammonium ion. Particular examples of initiator compounds include sodium tetraethyl borate and lithium tetraethyl borate, lithium phenyl triethyl borate and tetramethylammonium phenyl triethyl borate.

Abstract translation: 在粘合剂组合物中用作键合低表面能基底如聚烯烃的季铵硼盐作为聚合引发剂。 季硼盐具有式I的化合物，其中R 1是C 1 -C 10烷基，R 2， R 3和R 4可以相同或不同，是C 1 -C 10烷基， 烷基或C 3 -C 10环烷基，苯基或苯基取代的C 1 -C 10烷基或 C 3 -C 10环烷基，条件是R 1〜R 4中的任意两个可以任选地为 碳环，M + +是金属离子或季铵离子。 引发剂化合物的具体实例包括硼酸四乙酯和硼酸四乙酯锂，苯基硼酸三乙酯和苯基三乙基硼酸四甲基铵。

公开(公告)号：US06939932B2

公开(公告)日：2005-09-06

申请号：US10419202

申请日：2003-04-21

Applicant: Brendan J. Kneafsey ,  Gerry Coughlan

Inventor： Brendan J. Kneafsey ,  Gerry Coughlan

IPC: C07D203/08 ,  C07F5/02 ,  C07J41/00 ,  C08F4/00 ,  C08F4/52 ,  C08K3/38 ,  C08K5/3412 ,  C09J4/02

CPC classification number: C08F4/52 ,  C08F4/00 ,  C09J133/066 ,  Y10T428/31855 ,  C08F2220/1875 ,  C08F220/20

Abstract: Use of an initiator system comprising: a combination of an organoborane and a polyaziridine, in a ratio of aziridine groups to boron atoms of greater than 1.3:1, as an initiator of polymerisation in an adhesive composition for bonding a low surface energy substrate; provided that the initiator system does not contain more than a trace amount of a complex of organoborane with a complexing agent selected from: an amine other than a polyaziridine; a complexing agent comprising at least one hydroxide; a complexing agent comprising at least one alkoxide; or amidine complexing agent. An initiator system as described is of the formula VI: wherein R1 is C1-C10 alkyl, R2 and R3, which may be the same or different, are, C1-C10 alkyl or C3-C10 cycloalkyl, phenyl, or phenyl-substituted C1-C10 alkyl or C3-C10 cycloalkyl, provided that any two of R1-R3 may optionally be part of a carbocyclic ring; R5 is a polyvalent radical, R6 and R7 which may be the same or different are H or C1-C10 alkyl, particularly C1-4 alkyl, especially methyl, and y is a number of at least 2, particularly 2-4, especially 3, and the value of x multiplied by y is greater than 1.3. Particular examples of initiator compounds include, trimethylol propane tris(3-(2-methyl aziridino))propionate and trimethylol propane tris-3-N-aziridinyl propionate.

Abstract translation: 1.一种引发剂体系的用途，包括：作为用于粘合低表面能底物的粘合剂组合物中的聚合引发剂的氮丙啶与硼原子的比例大于1.3:1的有机硼烷和聚氮丙啶的组合; 条件是引发剂体系不含有微量的有机硼烷与选自以下的络合剂的络合物：除了多氮丙啶之外的胺; 包含至少一种氢氧化物的络合剂; 包含至少一种醇盐的络合剂; 或脒络合剂。 所述的引发剂体系是式VI：其中R 1是C 1 -C 10烷基，R 2， 其可以相同或不同，为C 1 -C 10烷基或C 3 -C 10烷基， 苯基或苯基取代的C 1 -C 10烷基或C 3 -C 12亚烷基或C 3 -C 10 - > -C 10环烷基，条件是R 1 -R 3中的任何两个可以任选地是碳环的一部分; R 5是多价基团，R 6和R 7可以相同或不同，是H或C 1〜 特别是C 1-4烷基，特别是甲基，Y是至少2个，特别是2-4个，特别是3个，和 x乘以y的值大于1.3。 引发剂化合物的具体实例包括三羟甲基丙烷三（3-（2-甲基氮丙啶））丙酸酯和三羟甲基丙烷三-3-N-氮丙啶基丙酸酯。

公开(公告)号：US20050154160A1

公开(公告)日：2005-07-14

申请号：US11003959

申请日：2004-12-03

Applicant: Brendan Kneafsey ,  Gerry Coughlan

Inventor： Brendan Kneafsey ,  Gerry Coughlan

IPC: C08F4/52 ,  C08F220/18 ,  C09J4/00 ,  C09J4/02 ,  B32B27/00

CPC classification number: C08F4/52 ,  C09J4/00 ,  Y10T428/31504 ,  Y10T428/31855 ,  Y10T428/31928 ,  Y10T428/31935 ,  C08F220/18

Abstract: Quaternary boron salts are used as initiators of polymerisation in adhesive compositions for bonding low surface energy substrates such as polyolefins. The quaternary boron salts are of the formula I wherein R1 is C1-C10 alkyl, R2, R3 and R4, which may be the same or different, are, C1-C10 alkyl or C3-C10 cycloalkyl, phenyl, or phenyl-substituted C1-C10 alkyl or C3-C10 cycloalkyl, provided that any two of R1-R4 may optionally be part of a carbocyclic ring, and M+ is a metal ion or a quaternary ammonium ion. Particular examples of initiator compounds include sodium tetraethyl borate and lithium tetraethyl borate, lithium phenyl triethyl borate and tetraethylammonium phenyl triethyl borate.

Abstract translation: 在粘合剂组合物中用作键合低表面能基底如聚烯烃的季铵硼盐作为聚合引发剂。 季硼盐具有式I的化合物，其中R 1是C 1 -C 10烷基，R 2， R 3和R 4可以相同或不同，是C 1 -C 10烷基， 烷基或C 3 -C 10环烷基，苯基或苯基取代的C 1 -C 10烷基或 C 3 -C 10环烷基，条件是R 1〜R 4中的任意两个可以任选地为 碳环，M + +是金属离子或季铵离子。 引发剂化合物的具体实例包括硼酸四乙酯和硼酸四乙酯锂，苯基硼酸三乙酯和硼酸四乙基铵苯酯。

公开(公告)号：US06844080B2

公开(公告)日：2005-01-18

申请号：US10399229

申请日：2001-10-23

Applicant: Brendan J. Kneafsey ,  Gerry Coughlan

Inventor： Brendan J. Kneafsey ,  Gerry Coughlan

IPC: C08F4/52 ,  C08F220/18 ,  C09J4/00 ,  C09J4/02 ,  B32B27/30

CPC classification number: C08F4/52 ,  C09J4/00 ,  Y10T428/31504 ,  Y10T428/31855 ,  Y10T428/31928 ,  Y10T428/31935 ,  C08F220/18

Abstract: Metal alkyl borohydrides are used as initiators of polymerisation, particularly in adhesive compositions for bonding a wide range of substrates including low surface energy substrates such as polyolefins. As described, the metal alkyl borohydrides are of the formula I or II. wherein R1 is C1-C10 alkyl, R2 and R3, which may be the same or different, are H, D, C1-C10 alkyl or C3-C10 cycloalkyl, phenyl, or phenyl-substituted C1-C10 alkyl or C3-C10 cycloalkyl, provided that any two of R1-R3 may optionally be part of a carbocyclic ring, and M+ is a metal ion. In particular, alkali metal trialkyl borohydrides are used, the alkali metal salt being selected from: Lithium triethylborohydride, Sodium triethylborohydride, Potassium triethylborohydride, Lithium tri-sec-butylborohydride, Sodium tri-sec-butylborohydride, Potassium tri-sec-butylborohydride, and Lithium triethylborodeuteride. Other exemplified compounds which are less effective on low surface energy substrates include Lithium 9-borabicyclo [3.3.1]-nonane (9BBN) hydride, Lithium thexylborohydride, Lithium trisiamylborohydride and Potassium trisiamylborohydride.

Abstract translation: 金属烷基硼氢化物用作聚合引发剂，特别是用于粘合包括低表面能底物如聚烯烃在内的各种基材的粘合剂组合物。 如上所述，金属烷基硼氢化物具有式I或II。其中R 1为C 1 -C 10烷基，R 2和R 3可以相同或不同，为H，D，C1- C10烷基或C3-C10环烷基，苯基或苯基取代的C1-C10烷基或C3-C10环烷基，条件是R 1 -R 3中的任意两个可任选地是碳环的一部分，并且M + 特别是使用碱金属三烷基硼氢化物，碱金属盐选自：三乙基硼氢化锂，三乙基硼氢化钠，三乙基硼氢化钾，三仲丁基硼氢化锂，三仲丁基硼氢化钠，三 - 仲丁基硼氢化钠和三乙基硼化钕。 在低表面能底物上效力较低的其它示例性化合物包括9-硼双环[3.3.1] - 壬烷（9BBN）氢化锂，三异丁基硼氢化锂，三氨基硼氢化锂和三丁基硼氢化钾。